Punched Card CO e for General Kesear c h
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KENNETH N. CARIPBELL AXD BARBARA K. CARIPBELL University of Notre D a m e , Notre D a m e , I n d . , a n d Indiana Cniuersity, S C J U LB~eLn d , I n d .
A punched card code for general organic research has been developed, based on the use of 5 X 8 inch Key-Sort cards. The essential feature of this system is a direct code incorporating the main functional groups of organic compounds and the most common reactions and techniques used iii
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E E P I S G abreast of the curient literature presents difficulties to the academic research chemist that troublc his industrial colleague t o a much less extent. The academic inan rarely has trained assistants to help him with the task, secretarial help is frequently rather limited, and most university libiaries do not furnish abstracting service. In addition to this, the research professor is apt to have a somewhat broader field of interest than the industrial man; he must watch for new data to incorporate in lecture notes and must also, like the industrial chemist, be always looking forpew ideas.
organic chemistry. A condensed author code is also included. By means of this system it is possible to abstract an entire journal article on one card, even though the article deals with several different points of interest, and find the card again under any of the subjects mentioned. CODED PUUCH CARDS
The best solution to this difficulty seemed t,o be the use of coded punch cards for recording literature data. After considerable investigation Key-Sort cards were chosen; these are 5 X 8 inches, Form K6-152, with a double row of holes acros3 the top and bottom and a single row of holes a t each side (McBee Company, 295 Madison Ave., Kew York l i , N. Y.). They were chosen for the following reasons:
S o mechanical punching or sorting device is necessary. Several kinds of hand punches are available. One of these clips out both holes of a pair and mother clips the outer hole only. A slotting punch also is available, which can be used to notch the inner hole without cutting the outer hole of a pair. Cards so punched fall below the level of unpunched cards on the needle but do not fall off'. Use of such a slotting punch would require revision of the code described here. Sorting can be done very simply with a needle resembling a knitting needle. The 5 X 8 inch cards provide plenty of room for a fairly dctailed abstract of a journal article, because both sides of the card can be used, and the number of holes available permits fairly detailed coding. Mistakes in punching can be coirected by use of gummed-papcr correctors available from the hlcBee Company.
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Figure 1.
Code for Authors' Research Work
The present authors have found it desirable to keep a iairlx. detailed reference file on all their research problems, because student bibliographies and student abstracts are not always adrquate, and also to keep a file on important points of technique. When a research student gets in difficulties, he can bc given a few key references to read, and when he is running a reaction new to him, he can be given references to the technique of that reaction, if it is not covered in the standard reference books. The major difficulty has been the filing of a reference so that it can be found again. Journal articles frequently deal x i t h two or more problems, or contain several rather unrelated points of interest. If a journal article is abstracted on a single card, and filed unQr one heading, that reference is effectively lost as far as the other pertinent headings are concerned. One solution is to make several copies of the card, so that one copy can be filed under each appropriate heading. This, however, involves considerable secretarial work, leads to a very large and unwieldy file system, and in the authors' experience, does not really solve the problem.
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The Mannich bases from the a c e t a t e esters or a c e t y l e n i c alcnhals on c a t a l y t i c hyerogenation a t room temperature and moderate pressure absorb
moles o f hydrogen t o saturate the t r i p l e bond end remove
the OH group.
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If the hydrogenation i s interrupted a f t e r the absorption o? one r o l e , then the oleCinlc m i n o alcohol e s t e r is obtained.
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In the present authors' opinion, these stock Form KS-152 cards are very satisfactory and much cheaper than any specially designed literature punched cards; the numbers under the holes can be disregarded. A code system was wanted that would meet the following requirements:
A single card for each journal article. 4 n y system requiring several cards for an article, or one card per compound, involves too much labor.
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INDUSTRIAL AND ENGINEERING CHEMISTRY
A single code, to cover all fields of interest. A system flexible enough to include data for lectures as well as for research, and one that could be expanded to cover future fields of interest. Although several excellent articles and one very comprehensive bibliography (1-3) on punched card systems have been published, the authors were unable to find any description of a code system resembling the one they wanted. The code developed to meet the above requirements may serve in some degree as a guide to others faced with similar literature problems. No two research ehemists will find any one code equally satisfactory to both; nonetheless, they can utilize many of the basic principles of the same system.
0-AcetYlamino-4-hydrowquinaldine (1) was prepared from p-acetylcminoaniline and acetoacetic ester to the anilinocrotonate, followed by cyflization in DoWthem at 2400. Methylation or I with Me sullate in toluene gives chiefly the methvl methosulfate on the rin N* heating with dilute alkali causes reamgtt to the 4-Me0 cpd in BO-&%'yfelds. The 4-Me0 cpd with alc. ammonia at llOo or excess a m e n i m acctete at l85O iveS the 4 NR derivative 4,B-D~amino-2-methg~quinolin~& condensed with various acid chlorides in KOAQ soh. Reaction occurred on the 6-N& group and not the 4-nR2, as established by independent synthesis. Chlorides of malonic mbrtihrted malonfc, glutaric, adipic, pimelic and suberlc acids us:d. Products all inactive vs malonamidea active VI(. -weakly - active & a adipmlde stroncly active againit T., inactive aga nst
Figure 3.
Syntheses of Diaminoquinaldine
I n making up a code for one's research h-ork one of the most important things is to let the code "season" for a while before using it-make up a tentative codc, and then accumulate a rather large number of cards before punching them. I n this way any obvious errors or omissions in the code can be corrected before the cards are punched. It is most unsatisfactory to alter a code after several hundred cards have been punched under an inadequate system. The authors' tentative code was allowed to season for about 6 months, and then was revised to the one described here. This has been in use for 3 years, and has proved very satisfactory. It is shown in Figure 1. The author portion of the code is considerably abbreviated and codes only the initial letter of the senior author's surname. I n the authors' work, there has rarely been occasion to sort cards by author, and ralatively unskilled help can be used to put cards in alphabetical order when needed for a bibliography. I n making up the author code, the relative frequency of the initial letter of surnames was determined from the author portion of the Third Decennial Index of Chemical Abstracts. The letters used most frequently were given the code values easiest to punch. By combining some of the less common letters, it was possible to make up a satisfactory code using only six holes. There is no provision in the code for such information as type of publication, date, or oFiginal or secondary reference. These data are given on the face of the card. The main feature of the system is a direct code of the main functional groups found in organic compounds, which uses most of the holes across the top of the card. Because it is not possible to include all the functional groups or types of compounds in the space available, those of most interest were chosen; other workers would need t o modify this portion of the code to fit their own interests. Because this is a direct code, it is necessary to have some order of preference to serve as a guide when both the inner and outer holes of a pair are needed. In general, the more common groups or classes are given t o the inner, and the more rare t o the outer holes. Then if only the inner hole applies, both are
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punched out; if only the outer hole is needed, it is punched; but if both apply, still only the outer is punched. For example, if a reference deals with chlorides only, both holes are cut out, but if it deals with both chlorides and iodides only the iodide hole is clipped. I n thjs way it is easy to locate all the information on iodides, but if one is looking for data on chlorides, he will have t o go through the cards on iodides as well. Because the number of cards dealing with iodides is much smaller than that dealing with chlorides, this does not entail a great deal of extra labor. If the slotting punch is used, it is better to code the more common functional groups on the outside and the less common on the inside row; then use the slotting punch when only the inner hole of a pair applies, the single punch for the outer hole, and the double punch if both holes apply. The top rows also include holes to indicate whether the reference deals primarily with theory, with reactions, or with methods of preparation, and whether or not drugs, natural products, or polymers are involved. There is also indication of whether apparatus is described in the article. The right-hand row of holes is used to code the reactions t h a t may be described on the card. Here also, it is not possible to include all reactions, so they have been grouped. The hole assigned to the Grignard reaction is punched not only for references dealing with this reaction, but also when organolithium or organocadmium compounds are described. The hole assigned to the Friedel-Crafts reaction is also used for the Gatterman reaction and related reactions. The left-hand row of holes is used for coding special techniques. The bottom rows of holes are reserved for expansion, and for more detailed coding of special points. At present, one section of the bottom rows is being used to code types of synthetic drugs.
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Tables of absorption coefficient8 cf the following functional grouas ate siren:
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Alcohol, aldehyde, ketone, ester, carboxylic acid, and five types of RCK:CFb, &CiCKg, olefins: RCA:CARf, RCA:CAR*, R2C:CRR*
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The method can be used for the quantitative or semi-auantitative determination of these groups in mixtures.
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Figure 4.
Oxygenated and Olefin Compounds
With a code such as the one described, it is not possible to avoid all hand-sorting, but the number of cards that must be looked over to find the desired one is much less than formerly. An entire journal article may be abstracted on one card, even if it deals with several different points of interest, and that card found again regardless of the purpose for which it is needed. The code is supplemented to some extent by a rough classification in the files. For example, a t present all cards dealing with quinolines are kept in one section, and all those dealing with ethylenimines are in another section. This makes it simple to find all the information on the quinoline nucleus or the ethylenimine nucleus, but if one is searching for data on the base-strength of amines, for example, it is necessary to sort, the quinoline cards as well as all the other cards. This rough type of classification can easily be altered from time to time to suit one's changing interests. A few illustrations of the use of the system are shown in Figures 2 to 4. The card in Figure 2 deals with esters of acetylenic amino alcohols and their hydrogenation. It has been punched for ali-
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INDUSTRIAL AND ENGINEERING CHEMISTRY
phatic, acetylenes, olefins, esters, alcohols, and amines, for reduction (catalytic), elimination reactions, and the Mannich reaction, and could he located again in a search for any of these types of compounds or reactions. Figure 3 shows a reference which concerns the. synthesis of diaminoquinaldine and derivatives thereof for testing as trypanocidal agents. It has been punched for preparation, drug% 6-ring, condensed ring, A--hetero (making up the quinoline ring system), keto ester, hydroxyl, olefin, amide, salts, and polyamine across the top, and for alkylation, condensation, displacement, ring closure, and rearrangement reactions along the right side.
Vol. 42, No. 8
Figure 4 shows a card which has been punched for aliphatic, olefin, alcohol, acid, ester, and carbonyl compounde, as well as for spectra, quantitative analyses, and identification. LITERATURE CITED
(1) Casey, Bailey, and Cox, J . Chem. Education, 23, 495 (1946). ( 2 ) Cox, Bailey, and Casey, Chem. Eng. ~Vews,23, 1623 (1945). (3) Ferris, Taylor, Perry, and Torok, “Bibliography on the Uses of Punched Cards,” 2nd ed., AMERICANCHEMICALSOCIETY,
Punched Card Committee, 1949. RECEIVED December 29, 1949.
Hicrofilm Selection Equipment in Information Vork H. T. ENGSTROM Engineering Research Associates, Znc., S t . P a u l , ,Ifinn.
A microfilm selector in the library of the Department of Agriculture is capable of scanning 70,000 index entries per minute, and future equipment will strive for greater
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T IS an axiom of well managed research that relevant informa-
tion available in the literature should be studied and assimilated before a new project is undertaken. While bibliographic compilations (such as Chemzcal Abstracts and Engzneermg Abstracts) are very useful, the problem of locating all the relevant material on a given subject is a formidable one. The difficulties grow as the store of technical knowledge continues to increase. About 4000 hooks of scientific or technical importance appear each year, together 75ith over 7000 periodicals, of which over 50% relate to the chemical field. The problem is particularly acute in the present unsettled era, in which emergency conditions require that complex technological problems be solved with minimum delay. Rapid location of technical information is an important link in national defense. Difficulties in utilizing an ever-increasing store of knowledge have in the past profoundly influenced our basic methods of education. During the early years of this country’s history, educational procedure sought to cram into each individual mind as much information as possible. Gradually educational emphasis shifted from learning by rote to acquiring methods for locating desired information. As long as the total mass of technical information remained moderate in proportions, a search through a few standard textbooks and the indexes of a few journals of learned societies sufficed. K e have now entered another phase in which it is a major undertaking merely to inspect the information pertaining to a given subject. Getting a t desired information has become escessively expensive in terms of time and effort required on the part of skilled research personnel. MICROFILM SELECTOR
Fortunately, the same accelerated technological activity n-hich has created the problem has provided the means for its solution. Techniques developed in the fields of chemistry, optics, electronics, and photography have made it possible to construct equipment specially designed for ultrarapid searching of large masses of information. A particularly promising device is the microfilm selector, two somewhat different models of which have
adaptability. Experience indicates that equipment can be produced to meet the requirements of any coding method, proposed or foreseeable.
been constructed-the prototype developed a t the Massachusetts Institute of Technology by T’annevar Bush and a more recent model built by Engineering Research Associates, Inc., under contract with the Office of Technical Services of the Department of Commerce. The Department of Commerce machine, like the earlier Bush prototype, effects selection of desired items of information by photoelectrically scanning a specially prepared microfilm. An imaginary line running longitudinally down the film divides it into halves. On one half, the information, usually in abstract form, is entered on the film by the ordinary processes of microphotography. On the other half of the film, the successive index entries pertinent to this information are entered by coding each entry separately as a transverse double row of small opaque and transparent squares. The pattern of such squares within a double row signifies uniquely a single index entrv. I n operation, this master film is driven at a high rate of speed past an examining mask of black cardboard, in which holes are punched so as to provide a pattern n-hich is the inverse of that signifying the index entry being sought. When the pattern of the desired index entry is exactly matched by the searching mask--and only thenthe photocell scanning unit is momentarily blacked out. This actuates a flash photographv system which copies the associated item of information on an auxiliary reel of previously unexposed photographic film. Once a run is complete, the exposed section of the auxiliary reel is developed using well known methods. In this way, various items of information associated tTith any one index entry can be selected and photographic copies prepared on the auxiliary reel. The machine, in its existing form, scans some 70,000 index entries per minute. Tests have been made a t the library of the Department of Agriculture using a 2000-foot reel bearing 72,000 abstracts. Each abstract was accompanied, on an average, by six coded index entries. It has proved possible to scan this test reel completely in 6 minutes. All abstracts associated with any one index entry could be located without imposing any severe load on the electronics or mechanisms involved. With film of typical quality used by the motion picture i d u s t r y , the device operates in a thoroughly reliable fashion.
