Bibliographic Sources in Organic Chemistry

Knowledge and management of information sources is one of the basic pillars for the development of teaching and research work.

It is worth noting that the search, fast, reliable and as exhaustive as possible of the results generated by other research groups, currently or in the past, is essential for the development of scientific activity. In this sense, it is desirable that the student is familiar with the bibliographic search (primary literature, reviews, sources of summaries or abstracts, types of references, impact factor, etc.) and knows how to find information from a reference.

However, it is necessary to convey to the student the problem of exhaustive bibliographic coverage of a field of information. Thus, like all other scientists, organic chemists have at our disposal a vast amount of specialized bibliography that has increased in the last decades as much as in all previous eras.

It can be estimated that the overall volume of literature in the area of Organic Chemistry doubles approximately every 10 years and more seriously diversifies into a large number of new and highly specialized journals. The result of this situation is that more and more time is required to search for information and consequently less time is left for reading and research.

Primary sources of bibliographic information

They publish precise and direct information on original research results. They consist of research journals and patents.

Research journals

Scientific journals have been published for over a hundred years and are the most widely used means of communication to transmit original research results. The journal expresses, by virtue of its topicality, the state of science at a given time. There are a large number of journals that publish original articles in chemistry, but only about 60 are of general interest to most chemists.

Scientific work in the area of Organic Chemistry can focus on fields of great diversity, so a comprehensive list of journals, both general and specific, of interest to organic chemists can be found in the following link.

To this list could be added some journals dedicated to teaching aspects such as Anales de Química, the Journal of Chemical Education or Education in Chemistry, which can be of help on certain topics such as teaching methods, practical aspects, etc., with an interesting approach from the pedagogical point of view.

The contents of magazines can adopt three types of formats:

• Full papers. As the name indicates, the idea that gave rise to the work is developed until the proposed objectives are achieved. They provide detailed information on theoretical and practical aspects of the processes used and the compounds obtained.
• Short notes. These contributions are shorter than full papers, but have similar characteristics.
• Communications. They reflect in a condensed form the preliminary results of a relevant topic. They contain a minimum of experimental details, which are subsequently included in the elaboration of the full paper.

Patents

Patents are an important part of the bibliography, which can be accessed through the Official Gazzette of the US Patent Office. In addition, their abstracts are included in Chemical Abstracts. However, these sources are little consulted in academic circles, mainly due to the scarce and incomplete information they provide (in order to protect the process they purport to describe).

Numerous free patent databases are available online such as:

– USPTO patent databases. Bibliographic, citations, and full-text from 1976-
– PCT Gazette. Various full-text sources, 1997-
– Esp@ceNet. European patent office with pdf files of complete patents, including American patents.
– DEPATISnet. Especially suitable for German patents.

Technical reports and other contributions

Technical reports are non-periodical publications originating from public or private institutions where some type of research is being carried out. They are of little interest to the organic chemist. Technical publications originating from companies that manufacture material and equipment for scientific use are generally of greater significance. Some notable examples are the journals Aldrichimica Acta, Bruker Report, or Janssen Chimica Acta.

The Bachelor’s Theses and Doctoral Dissertations are an important source of primary information but very limited in their use due to distribution difficulties.

Secondary sources of bibliographic information

They include all publications that collect material that has been previously published in primary sources, i.e., abstracts, reviews, monographs, specific treatises, general treatises and textbooks, among others.

Summary information on original works

Given the great breadth and extent of primary sources nowadays, abstract journals greatly facilitate the bibliographic search, allowing us to access the content of journals that are not available in the immediate environment.

Among the most important publications of this type, dedicated to covering the general chemical literature, are the Chemical Abstracts (USA) and Refeativnij Zhurnal Khimiya, its equivalent in the area of influence of the former USSR, which began publication in 1953.

• Chemical Abstracts (CA) is the leading journal of abstracts, published weekly by the American Chemical Society, and collects abstracts in English of almost all publications containing chemical information, approximately 40,000 periodicals from over 150 countries, patents from 26 countries, as well as books, conference and congress proceedings, and technical reports from all over the world. Abstracts appear three to twelve months after publication of the original paper and are grouped into 80 sections, of which sections 21-34 belong to the area of Organic Chemistry. Every six months a volume is completed with the revisions corresponding to that period, which includes alphabetical indexes of the authors with the title of the work (Author Index), patents (Patent Index), chemical substances (Chemical Substance Index), chemical formulas (Formula Index) and subjects (General Subject Index). Cumulative indexes are also published every ten years, and there is also an index guide to help the user find the appropriate index headings quickly and efficiently.

Although CA, along with Refeativnij Zhurnal Khimiya, are the only ones currently published, there were two other European abstract journals, Chemisches Zentralblatt and British Abstracts, which ceased publication in 1970 and 1954, respectively. These publications predated that of the AC and often provided more detail. Chemisches Zentralblatt was published under different names from 1830 to 1969. The British Abstracts published its abstracts in the Journal of the Chemical Society from 1871 to 1925, and was an independent publication from 1926 to 1953.

• The German publication Chemischer Informationsdients (ChemInform) is an abstract journal that publishes carefully selected abstracts of articles published in more than 250 international journals on a weekly basis, appearing two to three months after publication of the original paper. This publication has the advantage of using a very clear graphical presentation, including complete reaction diagrams, which saves a lot of time in bibliographic consultation. In addition, it has a special chapter dedicated to review articles.

Compilation of titles

Among the journals that only publish the titles of scientific articles, without any kind of summary or information about them, except for the name, volume, number, page and year of publication, we should highlight Current Contents and Science Citation Index, from the Institute for Scientific Information of Philadelphia (USA), as well as Chemical Titles, published by the Chemical Abstracts Service.

Current Contents (Physical, Chemical, and Earth Science) is a weekly publication that began in 1967 and collects the titles of papers published in about 800 journals related to Chemistry. Each issue has an index of important words taken from the titles and an index of authors. It includes a section, Current Books, in which newly published books and their contents are cited. Since 1990, this publication has also been available electronically (CD-ROM and Internet).

Chemical Titles has been published every two weeks since 1961 and also provides a list of titles published in more than 700 journals in the field of Chemistry. It is curious how the titles are listed, as they appear in alphabetical order of each word in the title, not including prepositions, articles or very common words such as synthesis, preparation, research, etc., this causes each title to be listed repeatedly. There is a second section, called bibliography, where the complete titles and authors are listed.

Science Citation Index (SCI) is a more complete and complex work, which reviews the content of a large number of journals, approximately 3,200, related to the natural sciences and technology. It appeared in the early 1960s and is structured in four major independent sections: citation index (Citation Index), index of institutions (Corporate Address Index), index of sources (Science Index) and thematic index of permuted terms (Permuterm Index). Among the great informative possibilities, it is worth highlighting the usefulness of searching for articles that cite a given article, which makes it possible to know all the groups working on a topic and that cite a fundamental reference in the same.

Topic abstracts

Current Chemical Reaction (since 1979 and published by ISI), Journal of Synthetic Methods (since 1975 and published by Deerwent Publication) and Methods in Organic Chemistry (since 1984 and published by the Royal Society of Chemistry) publish monthly titles of scientific articles concerning new synthetic methods. The latter also lists books and review articles in the field of synthetic Organic Chemistry.

Current Chemical Reaction (since 1979 and published by ISI), Journal of Synthetic Methods (since 1975 and published by Deerwent Publication) y Methods in Organic Chemistry (since 1984 and published by the Royal Society of Chemistry) publish monthly titles of scientific articles on new synthetic methods. The latter also lists books and review articles in the field of synthetic organic chemistry.

Index Chemicus (since 1960 and initially called Current Abstracts of Chemistry and Index Chemicus) is another ISI weekly publication, which provides summary information on the synthesis and structures of new compounds. Each issue contains five indexes: author, journal, biological activity, labeled compounds and non-isolated intermediates.
Natural Products Updates (since 1987 and published by The Royal Society of Chemistry) is a monthly compilation of results, in the field of natural products, together with structural formulae. It includes new compounds, structural determination, new properties and total synthesis, along with other topics.

Review articles

Reviews greatly facilitate the knowledge of a given subject, since the authors condense all available information on the subject, giving at the same time their own interpretation. Reviews are collected in certain books and specialized journals.

• Journals with review articles

The following table lists the most important journals for organic chemists that publish review articles. Some of the above-mentioned journals that also publish review articles, in some cases only one such article in each issue, have also been included.

• Book series with review articles

There are also other publications of similar content to these, but which appear at somewhat irregular intervals and generally in book format and bound in hardback. Some of these publish reviews in all fields of chemistry, others only in organic chemistry, and others are even more specialized. Examples of these are listed in the following table.

Table 3. Serial, non-periodic publications of review articles

Among them all, perhaps Organic Reactions should be singled out, as it is a very important classical reference source for all organic chemists. It contains review articles on general reactions, and includes extensive tables of their applications. At the end of each volume there are cumulative subject and author indexes.

• Lists of review articles

On the other hand, some publications provide lists of review articles in the field of organic chemistry, among them the Journal of Organic Chemistry, which every three months gives a list of review articles published in a large number of journals. In addition, some authors have published articles where classified lists of review articles of specific areas within Organic Chemistry can be found, such as Organometallic Chemistry and Heterocyclic Chemistry. Finally, it should be noted that there are publications devoted exclusively to compiling lists of review articles, such as:

Index of Reviews in Organic Chemistry by D. A. Lewis. The first volume published in 1971 covers publications from 1960 to 1970; the second volume (1977) covers publications up to 1976. Annual or biannual supplements appeared until 1985 when publication ceased.

Index to Scientific Reviews, which is semiannual, began to be published in 1974 and is similar to SCI but relates to review articles.

Monographs

Monographs are specific works on a single topic of study or research within Organic Chemistry, which contribute, together with articles, to the total documentation of this scientific area. Some of them are written by a single author and others have chapters by different authors, but carefully selected to cover a specific area.

These monographs cover most of the fields of organic chemistry and their number is so large that it is impossible to present a complete list of them here. Although some of them are listed in the following section, we highlight examples here to indicate the topics they cover:

• The Chemistry of Functional Groups, Patai, S.Wiley, 1972.
• The Alkaloids, D. R. Dalton, Marcel Dekker, Inc., 1979.
• The Chemistry of Heterocyclic Compounds, Taylor E.C., Wiley, 1968.

Some monographs, due to their length, are included among the general works in the collections section.

General works

This type of information source generally takes the form of encyclopedias, collections and compilations of data.

Encyclopedias and collections

There are a large number of multivolume treatises covering the entire field of Organic Chemistry. We have selected some of the most significant works which I order alphabetically according to the surnames of the publishers:

• Abel, E.W.; Stone, F.G.A.; Wilkinson, G. Comprehensive Organometallic Chemistry, (14 vols.) Pergamon, 1995.
• Apsimon, J. The Total Synthesis of Natural Products, (7 vols.), Wiley, 1973-1988.
• Baldwin, J.; Magnus, P. Tetrahedron Organic Chemistry Series, Pergamon, 1983.
• Barton, D.; Ollis, W.D. Comprehensive Organic Chemistry, (6 vols.) Pergamon, 1979.
• Bamford, C.H.; Tipper, C.F.H. Comprehensive Chemical Kinetics, Elsevier, 1969.
• Buehler, C.A.; Pearson D.E. Survey of Organic Synthesis, Wiley, 1970 y 1977.
• Coffey, C.E. Rodd’s Chemistry of Carbon Compounds, 2ª ed., (5 vols.) Elsevier, 1964.
• Elderfield, R.A. Heterocyclic Compounds, Wiley, 1950.
• Fieser, L.F.; Fieser, M. Reagents for Organic Synthesis, Wiley, 1967.
• Hanchh, C. Comprehensive Medicinal Chemistry, (6 vols.) Pergamon, 1989.
• Helmchen, G.; Hoffmann, R.W.; Mulzer, J.; Schaumann, E. Stereoselective Synthesis, Thieme, 1996.
• Herrmann, W.A. Synthetic Methods of Organometallic and Inorganic Chemistry, Thieme, 1996.
• Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W. Comprehensive Organic Functional Groups Transformations, (7 vols.) Pergamon, 1995.
• Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W. Best Synthetic Methods, Academic Press, 1985.
• Katritzky, A.R.; Rees, O.W. Comprehensive Heterocyclic Chemistry, (8 vols.) Pergamon, 1984.
• Katritzky, A.R.; Rees, O.W.; Scriven, E.F.V. Comprehensive Heterocyclic Chemistry II, Pergamon, 1996.
• Larock, R.C. (ISBN: 0-471-19031-4) Comprehensive organic transformations, 2a ed., VCH, 1999.
• Lehn, J.M. Comprehensive Supramolecular Chemistry, Pergamon, 1996.
• Lindberg, T. Strategies and Tactics in Organic Chemistry, (3 vols.), Academic Press, 1984-1992.
• Manske, R.H.F.; Cordell, G.A. The Alkaloids, Academic Press, 1950.
• Morrison, J.D. Asymmetric Synthesis, (5 vols.), Academic Press, 1983-1985.
• Nicolaou, K. C.; Hanko, R.; Hartwig, W. Handbook of Combinatorial Chemistry , Wiley, 2002.
• Padwa, A. Organic Photochemistry, Marcel Dekker, 1975.
• Paquette, L.A. Encyclopedia of Reagents for Organic Synthesis, (8 vols.) Wiley, 1995.
• Patai, S. The Chemistry of Functional Groups, Wiley.
• Pelletier, S.W. Alkaloids: Chemical and Biological Perspectives, (10 vols.) Pergamon, 1983-1996.
• Rahman, A.-U. Studies in Natural Products Chemistry, (6 vols.), Elsevier, 1988-1990.
• Sandler, S.R.; Karo, W. Organic Functional Groups Preparations, 2ª ed., Academic Press, 1983-1989.
• Simonson, Owen, Barton, Ross The Terpenes, Cambridge University Press, 1947-1957.
• Suschitzky, H.; Scriven, E.F.V. Progress in Heterocyclic Chemistry, Pergamon, (7 vols.), 1989-1995.
• Trost, B.M.; Fleming, I. Comprehensive Organic Synthesis, (9 vols.) Pergamon, 1991.
• Velluz, L. Cahiers de Synthése Organique, Masson et Cíe., 1957-1966.
• Verschueren, K. Handbook of Environmental Data on Organic Chemicals, 4ª ed., Wiley, 2001.
• Weissberger, A.; Saunders, W. II. Techniques of Chemistry, (21 vols.) Wiley, 1970.
• The Chemistry of Heterocyclic Compounds, (49 vols.) Wiley, 1951-1990.
• Wilkinson, G. Comprehensive Organometallic Chemistry, (9 vols.) Pergamon, 1982.
• (varios editores) Compendium of Organic Synthetic Methods, Wiley, desde 1971.
• (varios editores) Organic Synthesis, Wiley, desde 1921.

Textbooks

There are many excellent books on organic chemistry. Here we will list the classics, some of them are general, first courses and others cover more specific aspects.

• Carey F.A., Organic Chemistry, 5ª ed., McGraw-Hill, 2003.
• Carey F.A.; Sundberg, Advanced Organic Chemistry 3ª. ed. (2 vols.) Plenum, 1990.
• Carruthers, Some Modern Methods of Organic Synthesis, 3ª ed., Cambridge University Press, 1986.
• Ege, Organic Chemistry, 4ª ed., D.C. Houghton Mifflin, 1999.
• Fessenden, Fessenden, Organic Chemistry, 6ª ed., Brooks/Cole, 1998.
• Fox, Whitesell, Organic Chemistry, 2ª ed., Jones & Bartlett, 1997.
• J. Fuhrhop; J. Li, Organic Synthesis: Concepts and Methods, 3ª ed., Wiley, 2003.
• House, Modem Synthetic Reactions, 2ª ed., W. A. Benjamin, 1972.
• Ingold, Structure and Mechanism in Organic Chemistry, 2nd ed., Cornell University Press, 1969.
• Isaacs, Physical Organic Chemistry, Wiley, 1987.
• Jones, Physical and Mechanistic Organic Chemistry, 2nd ed., Cambridge University Press, 1984.
• Jones, Organic Chemistry, W.W. Norton, 2000.
• Loudon, Organic Chemistry, 2ª ed., Benjamin/Cummings, 1988.
• Lowry and Richardson, Mechanism and Theory in Organic Chemistry, 3ª ed., Harper & Row, 1987.
• McMurry J., Organic Chemistry, 5ª ed., Brooks/Cole, 2002.
• Maskill, The Physical Basis of Organic Chemistry, Oxford University Press, 1985.
• Morrison, Boyd, Organic Chemistry, 6ª ed., Prentice-Hall, 1992.
• Pine Organic Chemistry, 5ª ed., McGraw-Hill, New York, 1987.
• Ritchie, Physical Organic Chemistry, 2ª ed., Marcel Dekker, 1989.
• Solomons, Fryhle, Organic Chemistry, 7ª ed., Wiley, 2000.
• Smith, Organic Synthesis, 2ª ed., WCB, McGraw-Hill, 2001.
• Smith; March “March’s Advanced Organic Chemistry: Reactions, Mechanism, and Structure” 5ª ed., Wiley, 2001.
• Streitwieser; Heathcock, Introductory Organic Chemistry, 3ª Macmillan, 1985.
• Sykes, A Guidebook to Mechanism in Organic Chemistry, 6ª ed., Longmans Scientific and Technical, 1986.
• Vollhardt; Schore, Organic Chemistry, 3ª ed., W.H. Freeman, 1999.
• Wade, Organic Chemistry, 4ª ed., Prentice-Hall, 1999.

Data collections

There are many books in organic chemistry that are essentially compilations of data, and they are very useful, as they save a lot of time for the researcher. Among these, the Beilstein “Handbuch der Organischen Chemie” (Springer) stands out. Although there are four editions of the work, the first three are out of date. The fourth edition (vierte Auflage) consists of a main series (das Hauptwerk) and four supplementary series (erstes, zweites, drittes and viertes Ergänzungswerk), each consisting of 27 volumes. Volumes 28 and 29 are an index of subjects and an index of formulae, respectively.

The Beilstein provides a list of all known organic compounds collected in the literature from antiquity to 1959, although some series are incomplete. The compounds are grouped into three main divisions: acyclic compounds (volumes 1-4), carbocyclic compounds (volumes 5-16), and heterocyclic compounds (volumes 17-27). For each compound the following information is provided: all names, the molecular formula, the structural formula, a brief description of the methods of preparation, physical, chemical and biological properties, as well as, in some cases, physical properties of their derivatives. All this information is accompanied by the corresponding original bibliographic references and has been carefully checked. The basic organizational system of this manual is very complex and it is necessary to familiarize oneself with it beforehand in order to get the maximum benefit from it.

The following is a selection of other important data collection works:

• Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds, VCH, 1993.
• Buckingham, J. Dictionary of Natural Products, (7 vols.) Chapman & Hall, 1997.
• Buckingham, J. Heilbron’s Dictionary of Organic Compounds, 6ª ed., Chapman & Hall, 1982-1992.
• Buckingham, J.; Macdonald, F. Dictionary of Organic Compounds, (9 vols.) 6ª ed., Chapman & Hall, 1995.
• Buckingham, J.; Macintyre, J. Dictionary of Organometallic Compounds, Chapman & Hall, 1989.
• Budavari, S. The Merck Index, 13ª ed., Merck, 1996.
• Bycroft, B. N. Dictionary of Antibiotics and Related Substances, Chapman & Hall, 1987.
• Collins, P. M. Dictionary of Carbohydrates, Chapman & Hall, 1997.
• Dean, J. A. Lange’s Handbook of Chemistry, 14ª ed., McGraw-Hill, 1998.
• Dean, J. A. Handbook of Organic Chemistry, McGraw-Hill, 1987.
• Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds, Academic Press, 1975.
• Hancock, W. CRC Handbook of HPLC for the Separation of Aminoacids, Peptides, and Proteins, CRC, 1984.
• Harborne, J. B.; Baxter, H. A Handbook of the Natural Flavonoids, Wiley, 1999.
• Hill, R. A.; Makin, H. L. J.; Kirk, D. N.; Murphy, G. M. Dictionary of Steroids, Chapman & Hall, 1991.
• Horspool, W. M.; Song, P.-S. CRC Handbook of Organic Photochemistry and Photobiology, CRC, 1995.
• Howard, P. H. Handbook of Environmental Fate and Exposure Data for Organic Chemicals, (5 vols.) Lewis Publishers, 1997.
• Katritzky, A. R. Handbook of Heterocyclic Chemistry, Pergamon , 2000.
• Lenga, R. E. The Sigma-Aldrich Library of Chemical Safety Data, 2ª ed., Aldrich Chemical Company, 1988.
• Lenga, R. E.; Votoupal, K. L. The Sigma-Aldrich Library of Regulatory and Safety Data, Aldrich Chemical Company, 1993.
• Lide, D. R. CRC Handbook of Chemistry and Physics, 83ª ed., CRC, 2002.
• Lide, D. R. Handbook of Organic Solvents, CRC, 1994.
• Lide, D.R.; Milne, G. W. A. Handbook of Data on Common Organic Compounds, , CRC, 1995.
• Lide, D.R.; Milne, G. W. A. CRC Handbook of Data on Organic Compounds, , CRC, 1993.
• Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers, CRC, 1996.
• Serjeant, E. P.; Dempsey, B. Ionization Constants of Organic Acids in Aqueous Solutions, Pergamon, 1979.
• Stephen, H. T. Solubilities of Inorganic and Organic Compounds, Pergamon, 1982.
• Yalkowsky, S.H.; He, Y. Handbook of Aqueous Solubility Data, CRC, 2003.
• The Syracuse Research Corp. Handbook of Physical Properties of Organic Chemicals, CRC, 1996.
• Yannai, S. Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients, Chapman & Hall, 2003.

Spectroscopic Data Collection

• Hites R.A. Handbook of Mass Spectra of Environmental Contaminants, CRC, 1992.
• McLafferty, F.W.; Stauffer, D.B. Important Peak Index of the Registry of Mass Spectra Data, Wiley, 1991.
• McLafferty, F.W.; Stauffer, D.B. The Wiley/NBS Registry of Mass Spectra Data, Wiley, 2000.
• Pachler, K. G.; Matlock, F.; Gremlich, H.U. Merck FT-IR Atlas, VCH, 1988.
• Perkampus, H.H UV-VIS Atlas of Organic Compounds, VCH, 1992.
• Pfleger K.; Maurer, H.H.; Weber, A. Mass Spectra and GC Data, (4 vols.) 2ª ed., VCH, 2000.
• Pouchert C. J. The Aldrich Library of FT-IR Spectra, 2ª ed. (3 vols.) Aldrich, 1997.
• Pouchert C. J.; Behnke, J. The Aldrich 13C and 1H FT-NMR Spectra, Aldrich, 1992.
• Schrader, B. Raman/Infrarred Atlas of Organic Compounds, 2ª ed., VCH, 1989.
• Socrates, G. Infrared Characteristic Group Frequencies: Tables and Charts, 3ª ed., Wiley, 2001.