GENERIC SEARCHING R Y USE
OF
ROTATED FORMULA INDEXES
97
Generic Searching by Use of Rotated Formula Indexes* By EUGENE GARFIELD Director, Institute for Scientific Information, 33 South 17th St., Philadelphia 3, Pa Received Morch 13, 1962
The term, “generic searching,” is variously interpreted to mean classified, inon-specific, group or categorized searching. For research chemists, generic searches are a valuable tool. Structulrally related chemicals with a specified combination of functional groups, rings, or other desiderata used to code or describe chemicals, may be found in a more orderly fashion by generic searching. While many machine searching systems code molecular formulas, this information is rarely used in generic searches. The Chemical Biological Coordination Center (CBCC) file provided molecular formulas which were not used much in searching. Generic searching often is done on a less sophisticated level. For example, one researcher regularly looks for articles on new uses of lithium. Obviously, as a lithium manufacturer, his company is interested in finding new applications. Similarly, chemists in the missile propellant field are interested in all new boron compounds since many are valuable in the production of propellants. From my own experience, I have found that the conventional formula indexes of Chemical Abstracts and of Index Chemicus do not permit a convenient means of searching generically except for certain classes such as steroids (C17), etc. For example, a search for “all compounds in which phosphorus is attached to a t least five oxygen atoms” is completely impossible unless you search every page of the index. If L. Pauling and V. Schomaker had been able to make such a generic search, it might have avoided the need to retract statements made in a communication commenting upon the works of E. Ronwin. I n November, 1951, Ronwin published a paper in J . A m . Chem. S0c.l introducing a new structural formula for both ribo- and desoxyribonucleic acids. The structure had as its core a (P&)n polymer chain of phosphoanhydride links. By a theoretical treatment, Ronwin showed the formula to be compatible with available factual data concerned with the structure of nucleic acids. I n February, 1952, L. Pauling and V. Schomaker wrote in a communication to the editor’: “In the proposed structure for the nucleic acids each P atom has five 0 atoms attached to it, three of which bind it to adjacent P atoms, and two of which are in a OH group and a sugar ester group, respectively. There is, however, no precedent for a structure in which P is bonded to five 0 a t o m s . . . the ligation of five 0 atoms about each P atom is such an
’ Presented at the l4lst Kational Meeting. Amerlcan Chemical Societs. Divison of Chemical Literature. March 22. 1962. Washington. D. C
unlikely structural feature that the proposed phosphotri-anhydride formula for the nucleic acids deserves no serious consideration.” However, in the July, 1952, issue,’ they made a most gentlemanly retraction in a second communication: “Dr. Ronwin has now kindly informed us that he has become aware of earlier references in the literature to compounds to which structures have been attributed involving quinquepositive P bonded to five 0 atoms or to a total of five 0 atoms and similar atoms. Anschutz4 prepared four compounds to which he assigned structures involving ligation of five 0 atoms to a P atom . . . our statement that there is no precedent for a structure in which a P atom is bonded to five 0 atoms must accordingly be withdrawn.” Frankly I can’t recall how I even came across this interesting discussion. I was doing a search on a completelyunrelated matter. I t occurred to me a t that time that the retraction would have been unnecessary-if a generic formula index to Chemical Abstracts were available. I was intrigued to learn how Dr. Ronwin managed to find the reference to Anschutz’s paper and others mentioned by Pauling. I t had been impossible for me to find them in a search. I wrote to Dr. Ronwin’ and asked him how he had managed to find the necessary precedent. Dr. Ronwin replied6 that a colleague had remembered the paper as an abstractor for Chemisches Zentralblatt! I n a subsequent letter, however, Prof. Pauling pointed out that the retraction did not involve a retraction of the criticism of the proposed phospho-tri-anhydride formulas for the nucleic acids. The retraction was limited to the statement that “there is no precedent for a structure in which a P atom is bonded to five 0 atoms.” Prof. Pauling correctly states that there might be some question about the correctness of the structures assigned to some of these compounds, and especially that these compounds are extremely sensitive to moisture.’ This, then, is the explanation of why and when I first felt the need for a rotated formula index. I wonder to this day whether there might not have been other examples in the literature which Pauling or Ronwin might have found if a rotated index were available. This example illustrates very well the role that new scientific information services can play in advancing scientific theory. In a short paper such as this, there is little need to belabor the question of the potential value of generic indexes. However, generic formula indexes may not be sufficiently appreciated as a searching tool since they have not, until now, been made available.
98
EUGENE GARFIELD
In previous papers, Skolnik’ and Fletcherg have indicated that conventional formula indexes leave much to be desired. They have shown how an “inverted” filing system with carbon and hydrogen given the lowest filing priority can be useful, not only in shortening the search for a specific compound, but also in locating generically related compounds. I n the Skolnik system used a t the Hercules Powder Co., elements are filed alphabetically with carbon a t the end of the formula and hydrogen completely ignored. In this system structural formulas are available on the file cards. At American Cyanamid, the Fletcher system, based on the periodic order of the elements, is used. I t has many definite advantages for grouping together structurally related chemicals. Dyson” also used a similar method. However, in any of these systems, there is only one file assignment made for each chemical. I n order to find a particular compound, it is necessary to anticipate all possible positions where a particular element might occur. For example, if a chemical contains both aluminum and phosphorus, and the chemist is searching for phosphorus compounds, he may not find i t under P, but rather under Al. I n previous papers that I have presented before this Division, I discussed the methods employed in preparing the molecular formula indexes to Index Chemicus.” ’’ Briefly, this involves the preparation of a single punchedcard for each formula. The cards are converted to magnetic tape and sorted on an electronic computer and printed on a high speed printer for photo-offset reproduction. Recently, over 150,000 formulas were processed in the preparation of our first two-year cumulation. I n this cumulation, we completely redesigned the index format to make it easier to use as well as to save space and lower costs. As a completely by-product operation, we have also prepared the first rotated formula index, a RotaForm Index. Let me first describe the RotaForm Index and then let me iliustrate its use with several examples. In Fig. 1,you see a typical page from the old cumulative molecular formula index to the Index Chemicus. As in Chemical Abstracts, the Hill system giving priority to carbon and hydrogen is used. All subsequent elements are filed alphabetically. However, a new heading has been created for each carbon-hydrogen combination to speed up locating a desired compound, simultaneously reducing the size of the index by about 25%. This can be seen by examining Fig. 2 which shows the new format. Notice the considerable amount of wasted white space below the carbon-hydrogen headings in the old format. The second major change in the format is the way that the serial numbers of the individual compounds are listed. Whereas each address was listed on one line on the left, they are now on the right of the molecular formula and one or more serial numbers appear after a dotted line. Notice in most cases that the line containing a new molecular formula is always justified on both margins. As I mentioned before, one card is prepared for each formula in the molecular formula index used now. T o prepare the RotaForm Index,the computer essentially duplicates the card as many times as there are different elements. If the compound contains, in addition to C and H , five other different elements, the formula will be repeated in the index five times. Thus, C23 H20 A12 Br3 F4 Na2 P 3 (hypothetical example) would be repeated in
the RotaForm I n d e s five times, once each under the following arrangements:
(1) A12 Br3 F4 Ya2 P3 C23 H 2 0 (2) Br3 A12 F4 Na2 P3 C23 H20 (3) F4 A12 Br3 Na2 P3 023 H20 (4) Na2.412 Br3 F4 P3 C23 H20 ( 5 ) P3 A12 Br3 F4 Na2 C23 H20
With this type of index, a search for compounds containing any one of these elements is possible in a quick and orderly fashion. Fig. 3 is a page from the new RotaForm Index. This page contains all the formulas containing three phosphorus atoms. Since all of the elements are sorted alphabetically, i t is a simple matter to locate, for example, all compounds containing three phosphorus atoms and also containing fluorine. These are found by scanning all of the P3 compound listings until P3 F12. There cannot be any fluorine compounds beyond this group because of the alphabetical arrangement. Seven such compounds have been checked. A similar search for P4 compounds containing fluorine is also shown. Four such compounds were located. There are some obvious advantages of the RotaForm Index. I t will now be quite easy t o determine, for example, all reported compounds containing a particular element such as boron. Much more sophisticated generic searches can also be done, as shown in Fig. 4. (Dr. Joe Clark of Lederle Laboratories kindly supplied the questions and the searches were conducted by members of the Index Chemicus staff: Mrs. Eleanore H. Peitsch Baus, Assistant Managing Editor, and George F . Corkery, Indexer, and Miss Sandra Goldman, Secretary). The RotaForm Index is a supplementary tool to the conventional formula index. I t permits a limited range of generic searches and is particularly valuable for a search involving the less-frequently occurring elements. I t is somewhat more cumbersome for searches involving 0, N , and S. Even these, however, can be performed with amazing results considering the low cost involved. The RotaForm Index is not a panacea for the problems of generic searching. I t is, however, one more tool t o add to the chemist’s armamentarium. I t is a by-product of our regular formula indexing, and completely machine-made. I t simply advises the reader which molecular formulas contain a particular combination of elements. I n order to keep the size down, we have not repeated serial numbers, which can be found in the molecular formula index. The searcher will save considerable time if he arranges molecular formulas found in the RotaForm Index by the number of carbon atoms before looking up the serial numbers. This is strictly a clerical procedure. I n fact, any use of the RotaForm Index can be assigned to a clerk until the final screening of the structural diagrams. Keep in mind that the use of this system in the average company chemical file, as is the case in the Hercules and in the American Cyanamid System, each molecular formula card is accompanied by the structural diagram. Such a card filing system eliminates the chore of going from the compound serial number to a register showing the structural diagram itself.
GENERIC SEARCHING BY USE OF ROTATED FORMULA INDEXES
99
ORGANIC COMPOUXDS
CH
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7303- 5 7303- 6 7303-19 6340- 5 6053- 4 7076-20 7199- 1 7207- 2 7814- 2 5023- 7 5023- 9 7543- 1 5023- 8 7303- 1 7303- 2 7303-14 7303-15 6340- 7 5023-10 6853- 3 5023- 2 7 8 1 4 - 4C 7814- 1 6818- 3 7303- 9 7303-10 7303-24 7303-11 7303-21 6 3 3 5 - 3C 6959-13 7814- 3 7814- 5 7814- 6 6 9 14-26 6914-27 7303-25 bole- 1 6737- 1 5910- 1
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Fig. 1.-Old
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2 4804- 7 4850- 9 5530- 2 5824- 1 6063-10 6973-16C 3 U l O 5524- 2 7041- 1 7041-13 7041-16 6135- 1 6858-44 4670-15 6275- 1 7895- 1 6973510C 3 H l l 6913- 4 6973-14 6449- 1 7 1 3 7 - BC 3H12
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53
format of cumulative mc)lecular formula index
EUGENE GARFIELD
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