Volumetric Study of (3-Ethoxypropan-1-amine + Water) Mixtures

Article pubs.acs.org/jced

Volumetric Study of (3-Ethoxypropan-1-amine + Water) Mixtures between (283.15 and 303.15) K Maria Luísa C. J. Moita,† Lídia M. V. Pinheiro,‡ Â ngela F. S. Santos,§ and Isabel M. S. Lampreia*,§ †

Departamento de Química e Bioquímica, Centro de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, 1749-016 Lisboa, Portugal ‡ Research Institute for Medicines and Pharmaceutical Sciences (iMED.UL), Faculdade de Farmácia da Universidade de Lisboa, Avenida Professor Gama Pinto, 1649-003 Lisboa, Portugal § Departamento de Química e Bioquímica, Centro de Ciências Moleculares e Materiais, Faculdade de Ciências, Universidade de Lisboa, 1749-016 Lisboa, Portugal ABSTRACT: Experimental densities were obtained in the binary mixtures water + 3-ethoxypropan-1-amine, for the whole composition range and at temperatures between (283.15 and 303.15) K. Derived thermodynamic properties such as apparent molar, excess molar, and excess partial molar volumes have been calculated. Limiting partial molar volumes and isobaric expansions were obtained for the two components. Different patterns of molecular aggregation and hydration schemes were detected.

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INTRODUCTION Alkoxyamines, through their alkoxy and amine functional groups, are versatile compounds with great affinity for water and potential industrial application. In fact they have been used for the immobilization of various compounds such as biomolecules by means of condensation reactions with aldehydes or ketones forming oxime bonds, which increase their stability.1 Additionally, the strong electron-donor functional groups of alkoxyamines have also been largely used in polymer chemistry to produce sequence-controlled polymerization and cyclization reactions.2,3 As far as we are aware, only one volumetric study is reported in literature concerning aqueous mixtures of these compounds.4 Pursuing our volumetric studies devoted to molecular interactions in binary systems water (1) + amphiphilic (2), to study the influence of structure5,6 chain length7,8 and type of hydrophilic groups,5,6,9−11 we report density values of 51 aqueous binary mixtures of 3-ethoxypropan-1-amine (EPA), spanning the temperature range from (283.15 and 303.15) K, at 5 K intervals over the entire composition range. Excess molar volumes of the mixtures and apparent and partial molar volumes of both components, from 0 < x2 < 1, were derived. A correction for hydrolysis accordingly with a procedure previously described9,12,13 was applied to data at 298.15 K to assess the extent of this effect. Limiting excess partial molar isobaric expansions were also obtained. Based on prior findings about the ill-suited appliance of usual Redlich−Kister (R-K) method to fit excess molar volumes obtained in aqueous mixtures of amphiphile compounds,14,15 in the very water-rich region, a refined R-K method, which uses lower order equations to fit data at the aforementioned region, was applied. © 2012 American Chemical Society

Different patterns of molecular aggregation and hydration schemes due to changes in the balance between H-bonding and hydrophobic interaction as a function of composition and temperature were observed.

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EXPERIMENTAL SECTION Materials. 3-Ethoxypropan-1-amine (EPA), CAS Registry No. 6291-85-6, was obtained from Sigma-Aldrich with purity quoted >99 in mass percentage and used as received. The content in water determined by Karl Fisher method was found to be < 0.16 mass %. Ion-exchanged water of high-purity (resistivity, 18 MΩ·cm) was obtained from a reagent grade Milli-Q system, supplied by Millipore. Solution Preparation. All solutions were prepared by weight using tight closed measuring flasks, suitable to avoid evaporation.16 Corrections for buoyancy were performed. Uncertainties in solutions composition, expressed in mole fraction, and calculated by error propagation of the determined masses of the components were found to vary from 3·10−7 to 1·10−5, depending on the composition and amount of prepared solutions. Density Measurements. We used an Anton Paar vibrating tube densimeter, model DSA 5000M, for measuring densities at (283.15, 288.15, 293.15, 298.15, and 303.15) K with an associated standard uncertainty of 0.01 K and a stability of ± 0.002 K. Air and ultra pure water at 293.15 K were used as calibrating fluids as recommended by the manufacturer. The repeatability and standard uncertainty of density measurements Received: March 12, 2012 Accepted: July 2, 2012 Published: July 13, 2012 2290

dx.doi.org/10.1021/je3003578 | J. Chem. Eng. Data 2012, 57, 2290−2295

Journal of Chemical & Engineering Data

Article

Table 1. Experimental Density Data for the Binary System Water (1) + 3-Ethoxypropan-1-amine (2), from T = (283.15 to 303.15) K ρ/g·cm−3 x2

T = 283.15 K

T = 288.15 K

T = 293.15 K

T = 298.15 K

T = 303.15 K

0.000000 0.0001081 0.0003191 0.0006252 0.0007066 0.0009424 0.0010461 0.0012843 0.0019472 0.002916 0.0039195 0.0050977 0.007456 0.009810 0.014804 0.019563 0.028319 0.039136 0.050821 0.066736 0.095356 0.120903 0.145154 0.184444 0.212076 0.243763 0.292341 0.361002 0.436854 0.493727 0.551304 0.621429 0.677529 0.694330 0.745814 0.773340 0.794733 0.827596 0.848775 0.874404 0.899316 0.918855 0.934910 0.941083 0.943586 0.948584 0.960131 0.961298 0.974599 0.975455 0.985043 0.987118 1.000000

0.999699 0.999685 0.999612 0.999489 0.999462 0.999378 0.999335 0.999244 0.999006 0.998665 0.998320 0.997943 0.997213 0.996579 0.995454 0.994585 0.993306 0.992137 0.991126 0.989564 0.985793 0.981126 0.976001 0.967807 0.960275 0.954343 0.944589 0.932627 0.921019 0.911932 0.904655 0.896914 0.891266 0.889590 0.884839 0.882976 0.880664 0.878228 0.876201 0.874608 0.872317 0.871084

0.999099 0.999073 0.998997

0.998203 0.998176 0.998098 0.997974

0.997043 0.997018 0.996937 0.996811

0.995643 0.995609 0.995522 0.995392

0.998755

0.997845

0.996670

0.995256

0.998623 0.998367 0.998003 0.997639 0.997245 0.996459 0.995782 0.994495 0.993456 0.991899 0.990361 0.988889 0.986858 0.982292 0.977267 0.971617 0.962845 0.955870 0.948987 0.939953 0.926801 0.916153 0.907295 0.900039 0.892186 0.886402 0.884998 0.880089

0.997706 0.997459 0.997058 0.996673 0.996250

0.996533 0.996269 0.995851 0.995450 0.995024

0.995106 0.994822 0.994409 0.993991 0.993550

0.994681 0.993269 0.992092 0.990264 0.988357 0.986504 0.983968 0.978874 0.973326 0.967737 0.958517 0.951456 0.944543 0.935456 0.922252 0.911545 0.902620 0.895311 0.887472 0.881634 0.880062 0.875436 0.873142 0.871067 0.868648

0.991796 0.990144 0.988708 0.986387 0.983868 0.981310 0.977903 0.971645 0.965331 0.959341 0.949751 0.942563 0.935550 0.926380 0.913059 0.902254 0.893262 0.885906 0.877992 0.872120 0.870586 0.865744 0.863589 0.861557 0.859105

0.864922 0.862730 0.861498

0.993348 0.991824 0.990530 0.988433 0.986207 0.983995 0.980975 0.975145 0.969369 0.963561 0.954192 0.947020 0.940074 0.930954 0.917676 0.906929 0.897985 0.890640 0.882775 0.876891 0.875446 0.870539 0.868397 0.866312 0.863952 0.862009 0.860155 0.858054 0.856710

0.859742

0.855013

0.850200

0.859290

0.854542

0.849691

0.858247 0.857315

0.853530 0.852649

0.848739 0.847719

0.856398 0.855715

0.851830 0.851018

0.846839 0.846075

0.875868 0.873430 0.871511 0.867858 0.866306 0.864955

0.869403

0.855327 0.853460 0.851896

0.864338 0.868869 0.868041

0.863267

0.866322

0.862192 0.861525

0.865360

0.860630

were found to be 0.005 and 0.02 kg·m−3, respectively. Due to the use of different batches of EPA, the density uncertainty of concentrated mixtures and pure EPA was found to be about 0.1 kg·m−3. All measurements were made at atmospheric pressure.

After setting the temperature and the cell being equilibrated, at each required value, density of the water was first measured, presenting differences to reference values17 always smaller than 0.01 kg·m−3. 2291



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of the Ak parameters and standard deviations of the fits are shown in Table 2.

RESULTS AND DISCUSSION Densities and Apparent Molar Volumes. Experimental density values, ρ, for the EPA aqueous system at (283.15, 288.15, 293.15, 298.15 and 303.15) K are summarized in Table 1. Apparent molar volumes, Vφ,2, (plotted in Figure 1 as a

Figure 2. Excess molar volumes, VEm, for water (1) + EPA (2) at: ●, 283.15 K; △, 303.15 K. Figure 1. Apparent molar volumes, Vφ,2, in the mixture water (1) + EPA (2) at: ×, T = 283.15 K; ▲, T = 288.15 K; ∗, T = 293.15 K; ●, T = 298.15 K and +, T = 303.15 K.

After observation of the apparent molar volumes at the water-rich region (Figure 1) and in accordance with previous evidence that a unique R-K equation, aiming to fit excess thermodynamic data across the entire composition range in water + amphiphile compounds, is in general ill-suited,15 we applied the technique of adjusting R-K equations of different order, at the water-rich region. A careful analysis revealed that a better description of the composition range up to x2 ≈ 0.015 (12 to 15 experimental points, depending on the isotherm) is obtained by R-K equations of a lower degree. In this case only two A′k coefficients (i.e., n = 1) were found to be justified. For comparison the inset of Figure 2 shows the two fits at 283.15 K in the very water-rich region, as an example, where the full and broken lines stand for R-K adjustments of first and eighth order, respectively. Ak′ shown in Table 2, are the parameters of eq 2 with n = 1 for the water-rich region. Negative VEm values were obtained, which do not vary significantly with temperature, except for the mole fraction interval 0.1 < x2 < 0.5, where more negative values are observed for the lower temperatures. This fact apparently indicates that the hydrophobic effect (more pronounced at lower temperatures), leading to the formation of amphiphile aggregates, can release some water molecules due to cosphere overlapping. Although apparent molar volumes give useful information about volume changes accompanying the mixing process, differential properties such as excess partial molar volumes are more efficient in separating the two component contributions and in describing volume changes associated with transitions in hydration or aggregation schemes, occurring across the entire composition range. Applying the cubic-spline method to VEm values, calculated with eq 3, we have therefore obtained dVEm/ dx2 derivatives to obtain excess partial molar volumes of the two components, VEi , using the following equations:

function of amphiphile mole fraction, x2) have been obtained by using eq 1, Vφ ,2 = [x1M1(ρ1* − ρ)/x 2ρρ1*] + M 2 /ρ

(1)

where M1 and M2 are the molar masses of components 1 and 2, respectively, and ρ*1 is the density of the pure water. In the water-rich region Figure 1 depicts maximum and minimum Vφ,2 values, similarly to what has been observed in the water + (diethylamine, DEA9 or 2-ethylaminoethanol, EEA8) mixtures and suggesting major changes in hydration patterns over the entire range of concentration. In the present case, maxima are displaced toward more dilute solutions in water (a closer view can be seen in the inset of this figure). Displacement of the maxima in the same direction is also disclosed as the temperature decreases. To better separate the contributions of the two components of the mixture, in the next subsection we direct our attention to excess partial molar volumes because these properties supply more valuable structural information. Excess Molar and Partial Molar Volumes. Excess molar volumes, VEm, were calculated from density values using eq 2, VmE = Vm − Vmid =

(x1M1 + x 2M 2) xM xM − 1 1 − 2 2 ρ ρ1* ρ2* (2)

where Vm and Vidm are the molar volumes of the real and ideal mixtures at the same composition, pressure, and temperature. The internal consistency and number of experimental points allowed choosing Redlich−Kister (R-K) equations of the form,

V1E = VmE − x 2dVmE/dx 2

n

VmE = x1x 2 ∑ Ak (2x 2 − 1)k k=0

(4)

and

(3)

V2E = VmE + (1 − x 2)dVmE/dx 2

to correlate VEm data. The statistical tool designated by F-test was used to optimize the number of Ak parameters to be used in eq 3. This number was found to be nine (n = 8) for the 283.15 K isotherm and eight (n = 7) for the other isotherms. Experimental and calculated (full lines) VEm values are shown in Figure 2, at the two extreme temperatures as examples. Values

(5)

VEi

The profiles of the curves, obtained at the two extreme temperatures, are represented in Figure 3. As has already been noticed for Vφ,2 isotherms, we denote that in the water-rich region the minimum observed in the VE2 curve is more pronounced for the lower temperature 2292



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Table 2. Least Squares Fitting Coefficients of Equation 3, Ak and A′k in cm3·mol−1, and Corresponding Standard Deviations of the Fits, σA and σ′A in cm3·mol−1, for the System Water + EPA, from T = (283.15 to 303.15) K A0 A1 A2 A3 A4 A5 A6 A7 A8 σA A′0 A′1 σ′A

T = 283.15 K

T = 288.15 K

T = 293.15 K

T = 298.15 K

T = 303.15 K

−8.5508 4.5363 −2.9650 −7.6189 5.0608 22.9077 −16.5353 −18.5287 15.6728 0.014 −55.92642 −46.70406 0.0004

−8.5349 3.8113 −0.1217 −3.4053 −9.6109 13.6074 10.3110 −12.0927

−8.5557 3.8157 −0.0790 −4.1031 −9.5735 13.8982 10.1913 −11.5913

−8.5339 3.7677 −0.1505 −3.9815 −8.2746 13.2623 8.7510 −11.0067

−8.5425 3.6420 −0.2858 −3.2519 −7.9174 9.9464 8.2396 −8.1354

0.014 −51.74279 −42.26283 0.0003

0.014 −45.59070 −35.76953 0.0004

0.013 −41.09093 −30.97358 0.0004

0.014 −37.54424 −27.13063 0.0002

subsequently, substituting VEm in eq 6 by the expression given in eq 3 and making xi tend to zero, VE,∞ can be expressed in terms i of the Ak coefficients. Resulting expressions, largely applied in the literature, are given by eqs 7 and 8. n

lim VφE,1 = V1E, ∞ =

x1→ 0

∑ Ak

(7)

k=0

and lim VφE,2 = V2E, ∞ = A′0 − A′1

x2 → 0

for

0 ≤ x 2 ≤ 0.0148 (8)

VEi ,

Figure 3. Excess partial molar volumes, for water (1) + EPA (2): thin , VE2 at T = 283.15 K; ---, VE1 at T = 283.15 K; thick , VE2 at T = 303.15 K; −··−, VE1 at T = 303.15 K.

Results are shown in Table 3 and Figure 4 jointly with standard uncertainties. Standard uncertainties have been calculated using the method explained in ref 15.

confirming the prevalence of the hydrophobic effect at the water-rich region. The displacement of this minimum toward x2 = 0, for the higher temperature, is better shown in this representation than in Figure 1. In addition, we can observe neat slope variations in the VEi vs x2 curve profiles, indicating some important changes in the aggregation patterns and/or hydration schemes. The compositions at which they occur seem to vary with temperature from x2 = (0.4 to 1), being more visible in the case of VE1 . To obtain limiting excess partial molar volumes at infinite dilution, VE,∞ i , we applied the R-K method (eq 3) to fit experimental excess molar volume data, using Ak (for VE,∞ 1 ) and A′k (for VE,∞ 2 ) coefficients of Table 2. Given that excess apparent molar volumes can be calculated from eq 6, VφE, i = VmE/xi

Figure 4. Limiting excess partial molar volumes, VE,∞ i , and respective error bars, for water (1) + EPA (2) as a function of temperature. upper E,∞ curve, VE,∞ 1 ; lower curve, V2 .

(6)

E,∞ Table 3. Limiting, Excess Partial Molar Volumes, VE,∞ i , and Their Standard Uncertainties, σ(Vi ), Calculated by Using Equations 7 and 8 for the System Water (1) + EPA (2) and for the Interval T = (283.15 to 303.15) K

a E,∞ V2

T/K

3 −1 VE,∞ 1 /cm ·mol

3 −1 σ(VE,∞ 1 )/cm ·mol

3 −1 VE,∞ 2 /cm ·mol

3 −1 σ(VE,∞ 2 )/cm ·mol

283.15 288.15 293.15 298.15 303.15

−6.02 −6.04 −6.00 −6.15 −6.30

0.03 0.09 0.08 0.08 0.08

−9.22 −9.48 −9.82 −10.12 (−9.5)a −10.41

0.05 0.04 0.06 0.06 0.04

corrected for hydrolysis at 298.15 K is expressed between parentheses. 2293



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Curve profiles of Figure 1, similarly to those observed in DEA,9 suggest that hydrolysis is acting in the very water-rich region. To assess how V2E,∞ values, calculated by the aforementioned process, are affected by hydrolysis, a different method starting from Vφ,2 values and corrected from hydrolysis has been used. The same procedure described in refs 12, 13, and 18 has been applied to Vφ,2 data, in the very-diluted region, at 298.15 K. Dissociation degree values, α, were determined from the basicity constant Kb = 1.3·10−4 at 298.15 K.19 The limiting partial molar volume of the cation BH+, V∞ BH+, was obtained from the group contribution values for the groups CH3, CH2, O, and NH3+, published by Gianni and Lepori20 and 3 −1 related to the convention V∞ H+ = −5.4 cm ·mol . Related to the ∞ 3 −1 same convention, VOH− = 1.36 cm ·mol , was obtained from 21 3 −1 V∞ OH− = −4.04 cm ·mol , published by Millero and related to ∞ value thus the convention VBH+ = 0. The corrected VE,∞ 2 obtained, at T = 298.15 K, is shown in Table 3 between parentheses. A difference of 0.6 cm3·mol−1 has been found, which is much smaller than that found for DEA at the same temperature (3 cm3·mol−1).9 Table 3 and Figure 4 display large negative values for both VE,∞ i , which show weak and large variations with temperature in the case of water and alkoxyamine, respectively. We attribute the significant negative slope of VE,∞ versus T to the decreasing 2 of the hydrophobic hydration, as the temperature increases. VE,∞ = −9.5 cm3·mol−1 found for T = 298.15 K is in close 2 agreement with the additive principle of interaction volumes claimed by Kharakoz22 taken into account three hydrogen bonds between the amine group (including the lone electron pair of the nitrogen atom) and water and one between the ether group and water, each of them producing a decrease in volume of 2.2 cm3·mol−1.22 Limiting Excess Partial Molar Isobaric Expansions. Limiting excess partial molar isobaric expansions, defined by the temperature derivative of limiting excess partial molar E,∞ volumes, at a fixed pressure, EE,∞ P,2 = (∂V2 /∂T)P, were then calculated to obtain a better evaluation of the solute−solvent interactions in the hydration cosphere, since the intrinsic volume is at least less expansible than the hydration cosphere. To fit the data a least-squares method was used, according to the following equation, V2E, ∞(T ) − V2E, ∞(293.15 K) = a(T − 293.15 K)

REFERENCES

(1) Hill, M. R.; Mukherjee, S.; Costanzo, P. J.; Sumerlin, B. S. Modular oxime functionalization of well-defined alkoxyamine-containing polymers. Polym. Chem. 2012, 3, 1758−1762. (2) St. Thomas, C.; Maldonado-Textle, H.; Rockenbauer, A.; Korecz, L.; Nagy, N.; Guerrero-Santos, R. Synthesis of NMP/RAFT inifers and preparation of block copolymers. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 2944−2956. (3) Nesvadba, P. N-alkoxyamines: Synthesis, properties, and applications in polymer chemistry, organic synthesis, and materials science. Chimia 2006, 60, 832−840. (4) Bulemela, E.; Tremaine, P. R. Standard Partial Molar Volumes of Some Aqueous Alkanolamines and Alkoxyamines at Temperatures up to 325 °C: Functional Group Additivity in Polar Organic Solutes under Hydrothermal Conditions. J. Phys. Chem. B 2008, 112, 5626− 5645. (5) Santos, A. F. S.; Moita, M. L. C. J.; Lampreia, I. M. S. Volumetric Properties of 1-propoxypropan-2-ol Mixtures between (283 and 303) K. The Effect of Branching on Alkoxyalcohols. J. Chem. Thermodyn. 2009, 41, 1387−1393. (6) Lampreia, I. M. S.; Santos, A. F. S.; Moita, M. L. C. J.; Figueiras, A. O.; Reis, J. C. R. Ultrasound Speeds and Molar Isentropic Compressions of Aqueous 1-propoxypropan-2-ol Mixtures from T = (283.15 to 303.15) K. Influence of solute structure. J. Chem. Thermodyn. 2012, 45, 75−82. (7) Barbas, M. J.; Dias, A. F.; Mendonça, A. F. S. S.; Lampreia, I. M. S. Volumetric Properties of 2-diethylaminoethanol in water from 283.15 to 303.15 K. Phys. Chem. Chem. Phys. 2000, 2, 4858−4863. (8) Lampreia, I. M. S.; Dias, F. A.; Mendonça, A. F. S. S. Volumetric Properties of 2-ethylaminoethanol in water from 283.15 to 303.15 K. Phys. Chem. Chem. Phys. 2003, 5, 4869−4874. (9) Lampreia, I. M. S.; Dias, F. A.; Mendonça, A. F. S. S. Volumetric Study of (Diethylamine + Water) Mixtures Between (278.15 and 308.15) K. J. Chem. Thermodyn. 2004, 36, 993−999. (10) Mendonça, A. F. S. S.; Dias, F. A.; Lampreia, I. M. S. Ultrasound Speeds and Molar Isentropic Compressions of Aqueous Binary Mixtures of Diethylamine from 278.15 to 308.15 K. J. Solution Chem. 2007, 36, 13−26. (11) Lampreia, I. M. S.; Dias, F. A.; Santos, A. F. S. Ultrasound Speeds and Molar Isentropic Compressions of Aqueous 2(Ethylamino)ethanol Mixtures from 283.15 to 303.15 K. J. Solution Chem. 2010, 39, 808−819. (12) Cabani, S.; Conti, G.; Lepori, L. Volumetric Properties of Aqueous Solutions of Organic Compounds. III. Aliphatic Secondary Alcohols, Cyclic Alcohols, Primary, Secondary and Tertiary Amines. J. Phys. Chem. 1974, 78, 1030−1034. (13) Kaulgud, M. V.; Bhagde, V. S.; Shrivastava, A. Effect of temperature on the limiting excess volumes of amines in aqueous solution. J. Chem. Soc., Faraday Trans. 1 1982, 78, 313−321. (14) Coquelet, C.; Awan, J. A.; Valtz, A.; Richon, D. Volumetric properties of hexamethyleneimine and of its mixtures with water. Thermochim. Acta 2009, 484, 57−64. (15) Santos, A. F. S.; Lampreia, I. M. S. How reliable are Extrapolations to Infinite Dilution of Partial Molar Properties using Redlich-Kister fittings? Thermochim. Acta 2011, 512, 268−272. (16) Barbosa, E. F. G.; Lampreia, I. M. S. Partial Molal Volumes of Amines in Benzene. Specific Interactions. Can. J. Chem. 1986, 64, 387−393. (17) Spieweck, F.; Bettin, H. Solid and Liquid Density Determination − Review. Tech. Mess. 1992, 59, 285−292. (18) Lampreia, I. M. S.; Ferreira, L. A. V. Thermodynamic Study of the Ternary System NaCl-H2O-Et3N at 25 °C. Part 1.−Volumes. J. Chem. Soc., Faraday Trans. 1993, 89, 3761−3766. (19) Nishikawa, S.; Haraguchi, H.; Fukuyama, Y. Effect of Ether Oxygen on Proton Transfer and Aggregation Reactions of Amines in Water by Ultrasonic Absorption Method. Bull. Chem. Soc. Jpn. 1991, 64, 1274−1282.

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E,∞ where a = VP,2 = −0.060 ± 0.001 cm3·mol−1·K−1 is independent of temperature. This negative value indicates that the EPA molecules have a larger expansion in their pure state than when they are infinitely diluted in water, due to the solute−solvent interaction.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel.: +351217500995. Funding

This work was funded by Portuguese national funds, through Fundaçaõ para a Ciência e a Tecnologia, part of it under projects PEst-OE/QUI/UI0536/2011 and PEst-OE/QUI/ UI0612/2011. M.L.C.J.M. and I.M.S.L. thank the University of Lisbon for granting sabbatical leave of absence in the academic year 2009/2010. Notes

The authors declare no competing financial interest. 2294



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(20) Gianni, P.; Lepori, L. Group Contribution to the Partial Molar Volume of Ionic Organic Solutes in Aqueous Solution. J. Solution Chem. 1996, 25, 1−42. (21) Millero, F. J. The Molal Volumes of Electrolytes. Chem. Rev. 1971, 71, 147−176. (22) Kharakoz, D. P. Partial Molar Volumes of Molecules of Arbitrary Shape and the effect of Hydrogen Bonding with Water. J. Solution Chem. 1992, 21, 569−595.

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Volumetric Study of (3-Ethoxypropan-1-amine + Water) Mixtures

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