Developing Students' Scientific Reasoning Abilities with an Inquiry

3 days ago - In this work we present an inquiry-based learning approach (IBL) where students are ... Hydrogen Bonding; Inquiry-Based Discovery Learnin...
0 downloads 0 Views 1MB Size
Laboratory Experiment Cite This: J. Chem. Educ. XXXX, XXX, XXX−XXX

pubs.acs.org/jchemeduc

Developing Students’ Scientific Reasoning Abilities with an InquiryBased Learning Methodology: Applying FTIR Spectroscopy to the Study of Thermodynamic Equilibria in Hydrogen-Bonded Species P. G. Rodríguez Ortega,*,† R. Casas Jaraíces,† Marta Romero-Ariza,‡ and M. Montejo† †

Department of Physical and Analytical Chemistry, Faculty Experimental Sciences, University of Jaén, E-23071 Jaén, Spain Department of Didactic of Sciences, Faculty of Humanities and Educational Sciences, University of Jaén, E-23071 Jaén, Spain



Downloaded via OCCIDENTAL COLG on March 26, 2019 at 17:25:35 (UTC). See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.

S Supporting Information *

ABSTRACT: Laboratory experiences are a key and integral part of the chemistry degree that are intended to provide the students the necessary training for laboratory work and improve their scientific reasoning/research abilities and their understanding of the uncertainty in experimental measurements. Despite the unquestionable capacity of hands-on laboratory experiences to achieve these objectives, there is a general concern that, on many occasions, students are still somewhat immature in their ability to think things through, even in the latter courses. Keeping in mind that scientific reasoning is innate in humans, the reason why even science students may lack this ability near the end of their academic undergraduate trajectory may lay in the way that many of these courses are designed, i.e., mainly as follow-up recipes of chemical processes that, in the best of cases, will ensure that the participants seek information and reflect on the theoretical aspects related to the experiments carried out. In this work we present an inquiry-based learning approach (IBL) where students are expected to use FTIR spectroscopy and apply thermodynamic concepts to study the equilibrium of formation of H-bonded dimers of benzoic acid in solvents of different polarity. KEYWORDS: Inquiry-Based Discovery Learning, IR Spectroscopy, Hydrogen Bonding, Upper-Division Undergraduate, Laboratory Instruction, Physical Chemistry



INTRODUCTION Noncovalent interactions, such as hydrogen bonding, and their role in biological activity, chemical reactivity, and solubility (among other properties) are a ubiquitous topic in any chemistry degree curriculum that can be addressed either in general chemistry or in more specific physical chemistry or biological chemistry courses, depending on perspective and focus. Moreover, because of the richness of the structural and conformational information they provide, along with their sensitivity to slight structural changes, vibrational spectroscopy techniques (e.g., FTIR) are ideal tools to follow experimentally the formation of hydrogen bonds. In fact, there are several proposals for laboratory work for upper-level chemistry students that require the use of FTIR as a tool to reach a deeper understanding of the phenomenon.1−3 Undoubtedly, when properly developed, laboratory activities have many benefits related to the improvement of meaningful learning, conceptual understanding, development of metacognitive skills and comprehension of the Nature of Science (NOS).4 However, more often than not, chemistry laboratory activities are conceived as follow-up recipes in search of a previously known result. Although commonly accepted by practitioners at different teaching levels, this type of approach © XXXX American Chemical Society and Division of Chemical Education, Inc.

lacks the necessary aspects to develop and improve critical and scientific thinking. This fact has been extensively investigated and discussed in the literature over the years, showing little relationship between laboratory experiences and student learning.5,6 On the other hand, inquiry-based learning (IBL)7 activities create the opportunity to expose students to the scientific method (i.e., observe, investigate, experiment, analyze results, and draw conclusions) by making them responsible for their own learning process in a semiguided way.8 They facilitate the acquisition of research skills while helping students to understand new concepts by searching for the answer to a research question previously formulated.9,10 Thus, the IBL proposals begin with the introduction of a question or problem that can be answered if the students carry out a procedure based on the scientific method.11 Ideally, the question should be of interest to students. This approach allows achieving learning outcomes related not only to the main topic of the IBL proposal but also to a plethora of valuable transferrable competences such Received: October 24, 2018 Revised: March 6, 2019

A

DOI: 10.1021/acs.jchemed.8b00875 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

Laboratory Experiment

Figure 1. Structure of the monomeric (a) and dimeric (b) forms of benzoic acid.

(Pm) and the one at lower energy is called the dimer peak (Pd). The separation between these two bands is ca. 20 cm−1 independently of the solvent used, and their relative intensities vary depending on the concentration of the solute. Conversely, in the spectrum of the solid, a unique broad band, considerably red-shifted as compared with the bands in the spectra of the solutions, will be observed. Thus, the concomitant presence of monomers and dimers of BA in moderately polar environments is easily observable when inspecting the 1600−1800 cm−1 region of the mid-IR spectrum of the sample in solution. A concentration-dependent study of the carbonyl region in different solvents according to the methodology reported elsewhere15−17 would allow the experimental determination of the equilibrium constant for the dimerization process, as well as the estimation of the fractions of monomers and dimers at a given concentration. For any given solvent, the equilibrium constant of the reaction of formation of the BA dimer (KD; expressed in molar concentrations) can be defined as the ratio between the molar concentrations of dimeric (D) and monomeric (M) forms according to

as the ability to prepare scientific reports, oral and written communication skills, and the capacity for teamwork. For these reasons, in this work we describe an IBL-based laboratory experiment focused in the study of the hydrogenbond dimerization of benzoic acid (BA) and the influence in the process of the polarity of the surrounding media. Our pedagogical goals are • To improve the understanding of hydrogen bonding and chemical equilibrium integrating structural, spectroscopic and thermodynamic concepts. • To stimulate the development of research abilities: bibliographic search, experimental design, interpretation of experimental data, scientific reasoning and elaboration of scientific reports. • To create a classroom climate that favors reflective and critic thinking, cooperative work, and communication.



THEORETICAL BACKGROUND It is known that the crystal structure of BA is formed by cyclic dimers12,13 (Figure 1) with equivalent H-bonds. Although their stability depends largely on the solvent,14 dimeric structures persist in low-polarity solutions. This fact can be justified to the students in terms of the balance between enthalpic factors (cleavage and/or formation of solvent−solvent, solute−solvent, and solute−solute interactions) and entropic factors related with the persistence of the dimers. Thus, in aprotic and moderately polar solvents, the increase in the entropy of the system that would imply the rupture of the dimers is partially compensated for by the strength of the cyclic hydrogen bond as compared with the van der Waals’ type solvent−solvent and solute−solvent interactions. Therefore, in nonpolar solvents, enthalpic factors would be expected to tip the balance of the dimerization process equilibrium toward the dimer (in fact, no evidence of the monomeric form of BA is detected in the IR spectrum of species in CCl4, see associated content). The evaluation of the dimerization equilibrium constant by means of the experimental methodology described below, would connect these merely qualitative considerations with a physical constant of the system. On the other hand, the magnitude of the BA self-aggregation process in aprotic solvents with sufficiently different polarities will be reflected in the wavenumber, intensity and shape of the IR bands assigned to the vibrational modes of carbonyl stretching (ν(CO)) of the monomeric and dimeric forms of the species. Therefore, in a medium that allows the coexistence of monomers and dimers, two separated ν(CO) bands will be observed, and their relative intensities will be strongly dependent on the relative proportions (fractions) of the monomeric and dimeric species. Due to the hyperconjugation that takes place between the H-donor and H-acceptor in the formation of the dimer, the ν(CO) band of the dimeric species appears red-shifted in comparison with the vibrational frequency for the unbound group (monomers). As mentioned above, the band observed at higher energy in the IR spectra of the solutions is the so-called monomer peak

M + M V D;

KD = [D] /[M]2

(1)

Regardless of the effect of specific solute−solvent interactions, KD will differ depending on the polarity of the solvent that will either hinder or promote the molecular association process.18 The estimation of KD by FTIR spectroscopy is performed following a methodology that involves the experimental determination of the integrated absorbance of the vibrational band assigned to the carbonyl stretching of the monomeric form, i.e., the so-called Pm, observed at different concentrations. The data obtained must fit the equation15 2KD c0 1 = + 2 εmlA m Am (εml)2

(2)

where c0 is the analytical molar concentration of the sample (mol L−1), Am is the integrated absorbance of the monomer band, εm is the molar absorptivity of the monomeric species, and l is the path length employed during measurements. Equation 2 relates the thermodynamic equilibrium constant of the dimer formation reaction to Beer−Lambert law and can be derived by following a mathematical treatment which is detailed in the Supporting Information (see section S3). The introduction of this mathematical expression could enable a discussion on the concept of molar absorptivity (ε(ν̃)) from which the students must understand that the use of integrated absorbances instead of just peak heights is mandatory due to the variation in peak widths of IR radiation. As a parallel activity, εm(ν̃P m) and εd(ν̃P d) values could be determined by calculating the integrated absorbances of both Pm and Pd bands (using an appropriate deconvolution software). Finally, KD can be used to obtain the monomeric and dimeric fractions of the species at any concentration, whose relation is described by the following equations:17 B

DOI: 10.1021/acs.jchemed.8b00875 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

Laboratory Experiment

Figure 2. Material describing a hypothetical scenario for unfolding the IBL activity.

fm + fd = 1

fm 2 =

solution in a 3:2 solvent mixture of CDCl3 and CD3CN, (5) the IR spectrum of BA in a 0.2 M solution in CD3CN, and (6) the IR spectra of the two solvents. The activity was divided into two distinct phases: (1) a socalled preinquiry phase, where the students had the opportunity to get in contact with the problem, and (2) an inquiry phase, where students put into practice their research abilities. During the preinquiry phase, the students were exposed to the situation represented in Figure 2. The students were asked to perform a thorough inspection of the IR spectra of the sample under the different conditions. In this phase, the students were encouraged to discuss all the data with their peers through a thorough analysis and comparison, with special emphasis on observing and gathering as much relevant information as possible about the problem presented (see associated Supporting Information for further details). Thus, this part of the experience already created a preliminary atmosphere of inquiry where students engaged in vivid scientific debates. Table 1 lists the different stages and instructions along with the student’s activities and the associated abilities and skills that the students are expected to develop in the context of this laboratory instruction. In the subsequent inquiry phase, the students were involved in an open experience. Thus, they were required to ask questions, formulate hypotheses related to the problem, search for scientific literature, plan an experiment to corroborate/discard hypotheses, develop the experiment, and analyze the results. This way, they reached conclusions that allowed answering the questions posed in Figure 2 (Q1 and Q2). Note that, in practice, the development of stages 1 and 2 was carried out

(3)

fd (1 + fd ) KDc 0

(4)

in which f m and fd are the corresponding molar fractions of monomers and dimers, respectively, and c0 is the analytical molar concentration of the self-associating species. The value of KD can be also used to estimate ΔG° of the process in each solvent through the van’t Hoff relation. The sign of ΔG° will inform about the thermodynamic spontaneity of the dimerization process in each solvent.



EXPERIMENTAL OVERVIEW The present laboratory experiment was conducted by chemistry students enrolled in “Applied Vibrational Spectroscopy” which is an optional upper-level course. All the participants already had basic notions about IR spectroscopy (general theoretical background, identification of IR signatures characteristic of the fingerprint region to identify functional groups and structures, and general knowledge about acquisition/manipulation/interpretation of data). The students worked in groups (2−3 people) and were exposed to a fictitious problematic situation that they were expected to solve, represented by the image depicted in Figure 2. Together with the card, each working group received data previously collected for the problem sample, namely, BA: (1) the IR spectrum of the pure solid, (2) the IR spectrum of a 0.7 M BA solution in a 3:2 solvent mixture of CDCl3 and CD3CN, (3) the IR spectrum of a 0.7 M BA solution in CD3CN, (4) the IR spectrum of BA in a 0.2 M C

DOI: 10.1021/acs.jchemed.8b00875 J. Chem. Educ. XXXX, XXX, XXX−XXX

Tasks and Activities

Summarize the results obtained and the methodology implemented. Judge critically the suitability of the proposal and the quality of the results. Reflect on the different factors affecting the phenomena studied for BA and transfer the acquired knowledge to other related situations.

Plan an experiment to investigate the formulated questions. Ask the teacher to provide you with the required materials to carry it out. Perform the experiment that you proposed. Take notes of all your observations. Discuss with your group whether your hypothesis is accepted or if, instead, needs to be reformulated.

(i) Design an experimental protocol that allow characterizing the processes taking place according to the scientific literature and the material resources available in your laboratory (i) Carry out the experiments, manipulate data according to the proposed methodology (using specific software), and analyze results. (ii) Check if the physicochemical magnitudes determined experimentally are consistent with your hypothesis and can justify the initial experimental observations. Elaborate a scientific report presenting your results.

Phase 1: Preinquiry Read carefully the card given to you and observe and describe in detail the data depicted in it. (i) Check and compare the spectra of the sample recorded for the pure solid and its solutions in a Analyze the data of the sample using appropriate software. 3:2 CDCl3/CD3CN mixture and CD3CN. (ii) Check the spectra obtained for different concentrations of sample in the same solvent. Phase 2: Inquiry Phase of the Experiment Ask questions connected to the problem and formulate a hypothesis that are aligned with your (i) Hypothesize about the plausible reasons for the differences observed among the set of recorded chosen question. spectra. (ii) Discuss and agree on the nature of the phenomena causing the differences. Perform a bibliographic search to obtain information about the phenomena and its experimental (i) Discuss which kind of physicochemical magnitude could account for the phenomena observed. (ii) study using IR spectroscopy. Propose strategies to determine it experimentally by IR spectroscopy, on the basis of a thorough bibliographic search.

Instructions

Presenting experimental results in a scientific manner.

Experimenting and analyzing the results.

Asking questions and hypothesizing Getting insight into the topic through bibliographic search and documentation Planning.

Observing and recording data and observations.

Abilities and Skills

a This IBL proposal has been designed according to Kipnis and Hofstein (ref 4) and considering the specialized research in the field suggesting that the best inquiry-based learning results are obtained when carrying out a guided IBL methodology.19 bMore concrete information and suggestions for the instructor are detailed in the Supporting Information. cDetailed description of all phases and stages is available as Supporting Information, section S4.

6

5

4

3

2

1

Stage

Table 1. Description of the IBL Scenario for Studying the Thermodynamic Equilibria of Hydrogen-Bonded Speciesabc

Journal of Chemical Education Laboratory Experiment

D

DOI: 10.1021/acs.jchemed.8b00875 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

Laboratory Experiment

Figure 3. Concentration-dependent study of benzoic acid in (a) CD3CN and in (b) 3:2 CDCl3/CD3CN mixture.

pretation of the full-range IR spectra of the sample. Nevertheless, the implementation of the activity as described here does not require the use of deuterated species. Similarly, all IR spectra can be recorded by using KBr windows instead of BaF2. Full details of material and equipment needed to implement the activity can be found as Supporting Information.

simultaneously by the students who analyzed, discussed, and hypothesized about the data as parallel tasks. During these first stages of the inquiry phase (stages 2−3), students reached an agreement about the nature of the problem: i.e., BA is prone to hydrogen-bonding dimerization in moderately polar environments, but the amounts of dimers and monomers in any given matrix will depend on the polarity of the solvent and the concentration of BA itself. By inspection of specific scientific literature, it was concluded that determining the equilibrium constant of the dimer formation reaction would help adequately explain the experimental observations. A bibliographic search driven by the teacher (that suggested the proper keywords in a nonexplicit manner; see Supporting Information for further details) enabled the students to document themselves to propose an extrapolation of experimental methodologies based on IR spectroscopy previously reported that can be implemented to characterize the equilibrium of formation of dimers by estimating the equilibrium constant in different environments. Each working group received a fresh BA sample (powder) and a set of different solvents to work with. The implementation of the experimental methodology was semiguided by the teacher, who suggested key operations to be considered by the students while performing the experiments and analyzing the results (see associated content for further details). Finally, the results were presented through a report and a brief presentation. The work was completed in a total laboratory time of ca. 270 min (divided into three separate sessions) plus ca. 270 min of in-class time. According to specialized research regarding inquiry-based teaching methods3 and the learning evidence after implementation, this IBL lab was consistent with the acquisition of metacognitive abilities.



HAZARDS AND PRECAUTIONS Students are required to work exclusively in the hood and to wear personal protective equipment: protective clothing, protective gloves, and safety goggles. Cautions! Benzoic acid: corrosion (GHS05) and health (GHS08) hazards; causes skin irritation (H315), causes serious eye damage (H318), and causes damage to organs through prolonged or repeated exposure (H372). Chloroform-d: health (GHS08) and harmful (GHS08) hazards; harmful if swallowed (H302), H315, causes serious eye irritation (H319), suspected of causing cancer (H351), may cause damage to organs through prolonged or repeated exposure (H373). Acetonitrile-d 3 : flammable (GHS02) and GHS08 hazards; highly flammable liquid and vapor (H225), H302, H319. In case of swallowing, inhaling, and/or contact with eyes, immediately call a poison center, doctor or physician, remove contact lenses (if applicable), and rinse cautiously with water for several minutes.



DISCUSSION To fully answer the questions in Figure 2, a concentrationdependent study of the IR spectra of the species in two solvents of different polarity, namely, a 3:2 CDCl3/CD3CN mixture (ε = 17.9) and acetonitrile-d3 (ε = 37.5) was carried out in the 1650− 1750 cm−1 region. An example of the data obtained by the students is shown in Figure 3. By exploring the IR spectra, qualitative evidence of the process of self-association (dimer formation) could be obtained, which could support the response given to Q1 during stage 2 (see Supporting Information). The process of obtaining quantitative information on the monomer/dimer fractions involved the calculation of the integrated absorbance of the bands of interest in the IR spectra of the different BA solutions, after Lorentzian curve fitting and deconvolution of the 1650−1750 cm−1 spectral region (see Supporting Information for further details of the procedure). Table 2 collects an example of the data obtained by the students. The data obtained were then fitted to eq 2, and the dimerization constant of BA in each solvent was obtained from the slope of the plot of c0/Am2 values versus 1/Am. An



MATERIALS AND EQUIPMENT Benzoic acid (BA, CAS Reg. No. 65-85-0, ACS reagent, ≥99.5%, Sigma-Aldrich), chloroform-d (CAS Reg. No. 865-49-6, 99.8% atom D, Sigma-Aldrich), acetonitrile-d3 (CAS Reg. No. 220626-0, 99.96% atom D, Sigma-Aldrich), and rectangular sealed Spectral system cell of 75 μm equipped with BaF2 windows were used. The measurements were carried out on a Burker Vertex 70 FTIR spectrometer equipped with a ceramic Globar source, DLaTGS detector, KBr optics, and its ATR accessory (for the collection of solid-phase spectra). Data processing was carried out by using OPUS software v. 7.2. Note that the spectra were recorded using deuterated solvents in order to avoid misinterE

DOI: 10.1021/acs.jchemed.8b00875 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

Laboratory Experiment

Table 2. Comparison of CO Stretching Band Values for Monomers of Benzoic Acid in Solvents

Table 3. Corresponding Calculated Experimental Values for Benzoic Acid Determined Using Equilibrium Constants of the Dimerization Reaction in Each Solvent

Am,b by Solvent c 0, mol L−1a

CD3CN

3:2 CDCl3/CD3CN Mixture

0.7 0.6 0.5 0.4 0.3 0.2

58.74 52.04 45.41 38.12 29.83 20.36

45.19 41.25 36.69 31.90 26.02 19.79

Calculated Fractionsb by Solvent Dimerization 3:2 CDCl3/CD3CN Mixture

CD3CN

a

c0 = initial concentration. bAm = integrated absorbance.

c 0, mol L−1a

f m, %

fd, %

f m, %

f d, %

0.7 0.6 0.5 0.4 0.3 0.2

81 83 85 87 89 92

19 17 15 13 11 8

57 59 62 66 70 75

43 41 38 34 30 25

a

c0 = initial concentration. bf m = calculated fraction of monomers; fd = calculated fraction of dimers.

example of the graphs obtained by the students is shown in Figure 4. Finally, it was possible to estimate the monomeric and dimeric fractions at a given concentration by using the KD determined experimentally to solve eqs 3 and 4. Table 3 collects some of the data obtained by the students. Please note that the values obtained of KD imply positive and negative values of ΔG° for the dimerization reaction taking place in CD3CN and the 3:2 CD3Cl/CD3CN mixture, respectively, which are consistent with the fractions estimated of monomers and dimers in each solvent. The dimerization equilibrium constants and the subsequent fractions of dimers and monomers obtained were used by the students to justify the concentration-dependent features observed in the carbonyl region of the IR spectra of BA in each medium. Therefore, Q2 in the initial card could be satisfactorily answered. As a final task, the students were encouraged to present their results and findings in a scientific manner, by elaborating a report and delivering a short communication, activities which favored a climate of debate and discussion in the classroom.

spectra of BA registered for the pure solid and in solution and analyzed the effect of the concentration and the polarity of the medium in the carbonyl region. The equilibrium constant of the dimer formation reaction was estimated by means of a spectroscopic method that allowed them to understand the origins of those differences. In general, students obtained consistent and repeatable results of BA KD values which agreed with data reported in the literature for related species. Based on the comments of the students and the instructor’s evaluation after the implementation, it was observed that this activity not only involved the students in an active and significant construction of knowledge related to key chemical concepts but also supported the appropriation of scientific practices, the development of a better understanding of the nature of science, and the acquisition of a deeper vision of the chemistry of hydrogen bonding and its study by means of infrared spectroscopy.





CONCLUSIONS We describe an educational proposal based on contemporary trends and research evidence in science education about the benefits of inquiry-based learning.9,16 This IBL activity was designed to promote critical thinking and problem-solving skills in students when dealing with a problematic situation that requires the meaningful application of spectroscopic and thermodynamic concepts related to hydrogen bonding and chemical equilibrium. During the exercise, which was conducted in the context of the course entitled “Applied Vibrational Spectroscopy” (upperlevel Chemistry degree), the students implemented basic procedures for structural determination using FTIR spectroscopy. They rationalized the differences observed in the IR

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.8b00875. Chemicals, disposables, instrumentation and equipment, instructor lab manual, notes and guiding suggestion for implementing the activity, and instructions for the students (PDF, DOCX )



AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected].

Figure 4. Data-fitting corresponding to the concentration-dependent study of the sample in (a) CD3CN and (b) 3:2 CDCl3/CD3CN mixture. The corresponding dimerization constants are depicted at the right bottom side of each graph. F

DOI: 10.1021/acs.jchemed.8b00875 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

Laboratory Experiment

ORCID

(15) Chen, J.-S.; Wu, C.-C.; Kao, D.-Y. New approach to IR study of monomer-dimer self-association: 2,2-dimethyl-3-ethyl-3-pentanol in tetrachloroethylene as an example. Spectrochim. Acta, Part A 2004, 60 (10), 2287−2293. (16) Kuppens, T.; Herrebout, W.; van der Veken, B.; Bultinck, P. Intermolecular Association of Tetrahydrofuran-2-carboxylic Acid in Solution: A Vibrational Circular Dichroism Study. J. Phys. Chem. A 2006, 110 (34), 10191−10200. (17) Rodríguez Ortega, P. G.; Montejo Gamez, M.; Márquez López, F.; López González, J. J. Solvent Effects on the monomer/HydrogenBonded Dimer Equilibrium in Carboxylic Acids: (+)-(S)-Ketopinic Acid as a Case Study. Chem. - Asian J. 2016, 11 (12), 1798−1803. (18) Dutkiewicz, M. Correlation between the dielectric solvent polarity parameter, β, and rate and equilibrium constants for various processes. J. Chem. Soc., Faraday Trans. 1991, 87 (16), 2589−2592. (19) Lazonder, N. G.; Harmsen, R. Meta-analysis of Inquiry-Based Learning Effects of Guidance. Rev. Educ. Res. 2016, 86 (3), 681−718.

P. G. Rodríguez Ortega: 0000-0002-9705-4528 Notes

The authors declare no competing financial interest.



ACKNOWLEDGMENTS R.C.J. acknowledges funding from the Spanish Andalusian Government for a contract supporting an internship in the Physical and Analytical Chemistry Department at the University of Jaén.



REFERENCES

(1) Albin, T. J.; Fry, M. M.; Murphy, A. R. Synthesis, Characterization, and Secondary Structure determination of a Silk-Inspired, SelfAssembling Peptide: A Laboratory Exercise for Organic and Biochemistry Courses. J. Chem. Educ. 2014, 91, 1981−1984. (2) Guerin, A. C.; Riley, K.; Rupnik, K.; Kuroda, D. G. Determining the Energetics of the Hydrogen Bond through FTIR: A Hands-On Physical Chemistry Lab Experiment. J. Chem. Educ. 2016, 93, 1124− 1129. (3) McEvoy, J. P. Characterizing Carbonyls with Infrared Spectroscopy: An Introductory Chemistry Experiment in a Molecular Bioscience Program. J. Chem. Educ. 2014, 91, 726−729. (4) Kipnis, M.; Hofstein, A. The Inquiry Laboratory as a Source for Development of Metacognitive Skills. Journal of Science Mathematics Education 2008, 6 (3), 601−627. (5) (a) Hodson, D. A critical look at practical work in school science. School Sci. Rev. 1990, 71, 33−40. (b) Hofstein, A.; Lunetta, V. N. The laboratory in science education: Foundations for the twenty first century. Sci. Educ. 2004, 88 (1), 28−54. (c) Lazarowitz, R.; Tamir, P. Research on using laboratory instruction in science. In Handbook of research on science teaching; Gabel, D. L., Ed.; Macmillan: New York, 1994; pp 94−127. (6) Clough, M. P. Learning and teaching in the school science laboratory: An analysis of research, theory and practice. In Handbook of Research on Science Education; Abell, S. K., Lederman, N. G., Eds.; Lawrence Erlbaum Associates: Mahwah, NJ, USA, 2007; Chapter: 15, pp 393−441. (7) Hutchings, B. Enquiry-based Learning: Definitions and Rationale, Centre for Excellence in Enquiry-Based Learning; University of Manchester: Manchester, U.K., 2007; http://www.ceebl.manchester.ac.uk/ resources/papers/ (accessed March 2019). (8) Prince, M. J.; Felder, R. M. Inductive teaching and learning methods: Definitions, comparisons, and research bases. Journal of Engineering Education 2006, 95 (2), 123−138. (9) Romero-Ariza, M. Inquiry-Based Learning: is there enough evidence of its benefits in science education? Revista Eureka sobre Enseñanza y Divulgación de las Ciencias 2017, 14 (2), 286−299 (and references therein). . (10) Dostál, J. Inquiry-based instruction: Concept, essence, importance and contribution; Univerzita Palackého v Olomouci: Olomouc, Czech Republic, 2015. (11) Colburn, A. Focusing Labs on the Nature of Science: Laboratories can be structured to help students better understand the nature of science. Sci. Teacher 2004, 71 (2004), 32−35. (12) Feld, R.; Lehmann, M. S.; Muir, K. W.; Speakman, J. C. The crystal structure of benzoic acidA redetermination with X-rays at room temperature; a summary of neutron diffraction work at temperatures down to 5 K. Z. Kristallogr. - Cryst. Mater. 1981, 157, 215−231. (13) Grabowski, S. J. Analysis of hydrogen bonds in crystals. Crystals 2016, 6 (5), 59−63. (14) Yamaguchi, S.; Tominaga, K.; Saito, S. Intermolecular vibrational mode of the benzoic acid dimer in solution observed by terahertz timedomain spectroscopy. Phys. Chem. Chem. Phys. 2011, 13, 14742− 14749. G

DOI: 10.1021/acs.jchemed.8b00875 J. Chem. Educ. XXXX, XXX, XXX−XXX