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Chemistry & Biochemistry: Organic Chemistry

Subject guide for chemistry and biochemistry

Locating Books

To locate books on your topic, use the UCSB Library Search. As a starting point, use a keyword search on the likely terms. You are unlikely to find references to a single compound, but may be able to find useful books on classes of compounds, such as esters, carboxylic acids, or polymers. For the most general case, use organic compounds. For synthesis information, combine the compound class term with synthesis. For properties, use the specific property name (e.g. solubility, spectra, toxicology.) For collections of data, use handbooks or tables. Examples: amines synthesis, organophosphorus toxicology, organic compounds handbooks

If nothing comes up, try a broader class term, or try your class term without a qualifier. When you find a relevant record, check its subject headings to see if there is alternative terminology you should try. Similarly, use keyword searches to find books on particular methods or reactions (e.g., addition reactions, ring formation). You may also want to browse in the book stacks.

  • Organic analysis: QD 271-272
  • Organic synthetic methods: QD 262 and QD 281.
  • Specific classes of compounds:QD 300-406
  • Organometallics: QD 410-412
  • Physical organic chemistry: QD 476

General Reference Works

"Comprehensive Chemistry" series
Comprehensive Heterocyclic Chemistry    Ref QD 400 .C65 1984
Comprehensive Heterocyclic Chemistry II    Ref QD 400 .C65 1996
Comprehensive Natural Products Chemistry    Ref QD 415 .C63 1999
Comprehensive Organic Chemistry    Ref QD 245 .C65
Comprehensive Organic Functional Group Transformations    Ref QD 262 .C534 1995
Comprehensive Organic Functional Group Transformations II  UCSB Only  Ref QD 262 .C534 2005
Comprehensive Organic Synthesis    UCSB Only Ref QD 262 .C535 1991
Comprehensive Organometallic Chemistry    Ref QD 411 .C65 1982
Comprehensive Organometallic Chemistry II    Ref QD 411 .C652 1995
Comprehensive Organometallic Chemistry III   UCSB Only Ref QD411 .C653 2007
Comprehensive Polymer Science    Ref QD 381 .C66 1989
Comprehensive Supramolecular Chemistry    Ref QD 411 .C66 1996
       (for cryptands and other host-guest molecules)

These sets from Pergamon Press contain excellent review articles on various aspects of their respective subjects, and make good starting points for new research. The oldest of these, Comprehensive Organic Chemistry, is becoming somewhat dated, but is still useful. Each set is organized into volumes on broad subject areas; it's best to consult the subject indexes to locate your topic. Most of the sets also have an excellent molecular formula index.

"Dictionary of Compounds" Series
These series are alphabetical lists of compounds, with excellent indexing (including synonyms, molecular formula, and CAS Registry Numbers). Each compound entry provides basic physical data, with references to other data, including methods of preparation. Note that for any given compound, much of the data is duplicated from one set to the other.

Dictionary of Analytical Reagents    Ref QD 77 .D498 1993
Dictionary of Antibiotics    Ref RS 431 .A6 D53 1988
Dictionary of Drugs    Ref RS 51 .D479 1990
Dictionary of Organic Compounds, 6th ed.    Ref QD 251 .D5 1996
Dictionary of Natural Products    Ref QD 415 .A25 D53 1994
Dictionary of Organometallic Compounds, 2nd ed.    Ref QD 411 .D53 1995
Dictionary of Organophosphorus Compounds    Ref QD 412 .P1 E36 1988
Dictionary of Steroids    Ref QP 752 .S7 D53 1991
Dictionary of Terpenoids    Ref QD 416 .C75 1991

All of the above "Dictionaries" are available online in "Combined Chemical Dictionary", a part of CHEMnetBASE (http://www.chemnetbase.com. In CHEMnetBASE, the dictionaries are searchable by chemical name, formula, physical properties and, with the proper browser plug-in, by structure or substructute.

Knovel.com UCSB Only (http://app.knovel.com/)
Knovel provides electronic versions of an extensive collection of reference works in chemistry, including several for organicl chemistry.  Data tables are numerically searchable, and some titles provide interactive tables, graphs and equations.

Organic Chemist's Desk Reference    Ref QD 246 .D5 1996 suppl. gives a user's guide to DOC, with abbreviations, definitions and some useful property tables.

Studies in Natural Products Chemistry    QD 415 .A2 S78 1988
An ongoing series of volumes of review articles, mainly dealing with synthesis, but also delving into the biological activity of a wide variety of natural products. UCSB currently owns volumes 1-18.

Chemistry of Heterocyclic Compounds    QD 400 .C5
This ongoing multi-volume series (over 56 volumes, some in multiple parts) covers heterocyclic chemistry in depth. Each volume is devoted to a different class of compound (by size and number of rings and number and type of heteroatoms.)

Porphyrin Handbook    Ref QP 671 .P6 P67 2000
Very up-to-date and comprehensive ten-volume work on the organic and organometallic chemistry and biochemistry of porphyrins.

Reaxys UCSB Only

  • Immense collection of chemical substance and reaction data for organic, inorganic and organometallic chemistry; combines the Beilstein, Gmelin, and Elsevier Patent Chemistry databases
  • Searchable by text term, structure or reaction diagram and/or numerical property values.

Synthetic Methods

Science of Synthesis UCSB Only
This is an electronic version of a handbook of organic synthetic methods, in two parts: Science of Synthesis contains 22 volumes, covering the fields of Organometallics; Hetarenes and Related Ring Systems; Compounds with Four Carbon-Heteroatom Bonds e.g. Carbonic Acids, Imidic Acids etc.; Compounds with Three Carbon-Heteroatom Bonds e.g. Nitriles, Isocyanides, and Derivatives, Amides and Derivatives, Peptides, Lactams, Thio-, Seleno- and Tellurocarboxylic Acids and Derivatives, and Compounds with Two Carbon-Heteroatom Bonds e.g. Ketones, and Heteroatom Analogues of Aldehydes and Ketones. It is browsable by the table of contents, and may be searched by chemical name or chemical structure.
The Houben-Weyl Archive (1909 to 2004) provides immediate access to 146 000 product specific experimental procedures, 580 000 structures, and 700 000 references in all fields of synthetic organic chemistry - dating back to the early 1800s. It may be browsed by table of contents, or searched for name reactions. Most of the earlier volumes are in German.

Organic Reactions   UCSB Only Ref QD 251 .O68
Annual publication with review articles on important synthetic methods. Articles are published in no particular order, but the series is well indexed, with cumulative author and chapter/topic indexes in each volume for all the preceding volumes. The online version is browsable by article title or reaction type, and is structure-searchable.

organic-chemistry.org (http://www.organic-chemistry.org/)
This useful free website contains includes hundreds of short reviews of organic synthetic methods (adding about four per month), lists of name reactions (including descriptions, reaction and mechanism diagrams and references), synthetic methods organized by type of bond formed, lists of protecting groups for common functional groups with stability data, as well as the ChemExper federated search of organic chemical supplier websites, and more.

Organic Syntheses
Available in print at SEL Refernce Area, Ref QD 262 .O68
Annual publication with tested syntheses of organic and organometallic compounds. Gives detailed descriptions of synthetic techniques, reagents, yields and safety aspects. It is well indexed by authors, compound names, reaction types, and molecular formulas.
The print collective volumes include revised and updated syntheses from annual volumes. There is a cumulative index for the first eight collective volumes.
The online version is freely available to the public and contains the contents of the entire series, up to one year before the present, searchable by chemical name, CAS Registry Number, other text terms, and by structure or substructure. Use of this excellent database requires a Java-capable browser.

Comprehensive Organic Name Reactions and Reagents   Ref QD 77 .W36 2009
This three-volume set lists reactions and reagents alphabetically, and provides a general descriptin of each, reaction diagrams, proposed mechanisms, modifications, applications, related reactions and examples, with extensive references.

Comprehensive Organic Transformations, 2nd ed.    Ref QD 262 .L355 1999
This newly-updated guide to functional group preparations by Richard C. Larock, is organized by the type of compound (e.g. alkanes, esters, nitriles), then by the method of preparation (reduction, alkylation), then by the type of starting material. Each section gives references to review articles, as well as a list of specific examples with references. This edition covers the literature up to 1995. The first edition, published in 1989, is available for check out.

Name Reactions: A Collection of Detailed Reaction Mechanisms, 2nd ed. UCSB Only (3rd edition is available in print at Ref QD 291 .L5 2006)
Reaction diagrams with mechanisms and references.

Name Reactions and Reagents in Organic Synthesis  UCSB Only  Ref QD 291 .N86 2005
Many reactions and reagents in organic synthesis have been named for their discoverers. This volume lists name reactions, with general scheme, mechanism and examples and name reagents, with uses, preparations, precautions and examples. Both sections have cross-references to March's Advanced Organic Chemistry (QD 251.2 .M37, which edition is unspecified) and the reagents section cross-references to Fieser and Fieser (see below.)

Organic Syntheses Based on Name Reactions UCSB Only Ref QD 262 .H324 2002
Structure diagrams, references and examples with reaction conditions and yields.

Fieser and Fieser's Reagents for Organic Synthesis    Ref QD 262 .F5
Classic series reporting on new reagents and new uses for old reagents. Alphabetical list of reagents, with author and subject index. Cumulative index for Vols. 1-12.

Encyclopedia of Reagents for Organic Synthesis    Ref QD 77 .E53 1995
This popular resource contains articles on the reagent use of hundreds of different chemicals. The articles give physical data and brief, but detailed description of uses. Excellent references and indexing (compound name, formula, type of reaction) Articles are arranged alphabetically by reagent name.  The online edition (e-EROS)  is an updated edition.We do not currently have access to the full text of articles in the Wiley Online Library site, though you may browse and search e-EROS. We do, however, have access to subsets of EROS available in electronic form via Knovel.com:

Physical Properties and Characterization

CRC Handbook of Chemistry and Physics   UCSB Only Ref Desk QD 65 .H3
One of the most familiar sources; it contains a variety of useful physical and chemical data, with some references. Tables are grouped in broad subject sections. The main table of organic compounds contains data on melting points, boiling points, density, refractive index and solubility, as well as cross-references to Beilstein and Merck and the CAS Registry Number. Structure diagrams are listed after the main table, and there are synonym and molecular formula indexes following the structures. Available online as part of CHEMnetBASE. The online version is searchable by chemical name, formula or physical properties. Many tables may be sorted by property.

Merck Index (http://www.rsc.org/Merck-Index/)  UCSB Only  Ref Desk RS 356 .M4
Published by Merck Pharmaceuticals, with data primarily on organics, strongest on drugs. It is organized by chemical name, usually the common or trade name. It includes physical data, preparation references, toxicity and uses. Merck is well-indexed, by Registry Number, molecular formula and synonyms. The online version may be searched by text terms or numeric properties, or by structure (with the appropriate browser plug-in.) Both print and online versions include a dictionary of name reactions in organic chemistry, with reaction diagrams.

Aldrich Catalog (http://www.sigmaaldrich.com/>)    TP 202 .A48, also uncataloged copies
In addition to serving as an alphabetical catalog of the chemicals available from Aldrich, it includes basic physical data, cross-references to Beilstein, Merck and Fieser, and safety information. It has indexes by molecular formula and CAS Registry Number. The online version is free, and contains the same data, plus links to Aldrich's FT-IR, Raman and NMR spectra, and Materials Safety Data Sheets.

Dean's Handbook of Organic Chemistry   UCSB Only Ref QD 251.3 .G65 2004
Contains a host of tables of organic chemical properties. In some respects it is more complete than the CRC above, and perhaps easier to use.

Organic Compounds Database http://www.colby.edu/chemistry/cmp/cmp.html
This database, compiled at Virginia Tech and made available by Colby College, provides physical data on a large number of organic compounds, including molecular weight, melting point, boiling point, index of refraction and UV absorption and mass spectral peaks. It is searchable by name, molecular formula or by data values for the above properties.

CRC Handbook of Data on Organic Compounds (HODOC)   UCSB Only Ref QD 257.7 .H36
This multi-volume set gives structures, basic physical properties of organic compounds and references to find compounds in Beilstein and to Sadtler spectra collections. Compounds are listed in alphabetical order by their CAS systematic names. It has indexes for synonyms, formulas, spectral peaks, and CAS Registry Numbers. Now in its 3rd edition. Available online as part of CHEMnetBASE, under the title "Properties of Organic Compounds",

Handbook of Physical Properties of Organic Compounds    Ref QD 257.7 .H374 1997
This single volume work gives structure and data important to environmental fate of compounds (mp, bp, water solubility, octanol-water partition coefficient, vapor pressure, pKa, Henry's Law constant, and atmospheric hydroxyl radical reaction rate constant), and references. It is arranged by CAS Registry Number, with name and molecular formula indexes.

Cambridge Structural Database (WebCSD) UCSB Only  Produced by the Cambridge Crystallographic Data Centre, the Cambridge Structural Database is the world's repository of experimentally determined organic and metal-organic crystal structures, with over 500,000 structures.  The WebCSD interface allow for text and numerical searching, substructure searching, similarity searching, and reduced cell seaching of the database.  It can display structures in a variety of visualization formats.  WebCSD is paid for by the UCSB Department of Chemistry and Biochemistry; students in that department may contact departmental IT support for information on downloading additional CSD software.

Spectra: For Spectra sources, see the appropriate section of the General Chemistry guide.

For sample problems in organic compound characterization, try these sites:

WebSpectra (http://w3.chem.ucla.edu/~webspectra/)
This UCLA website has 75 compounds of varying levels of difficulty.

Organic Structure Elucidation (http://www.nd.edu/~smithgrp/structure/workbook.html)
This site from Notre Dame has 64 problems of varying levels of difficulty.

Locating Articles

Subject Guide

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Chuck Huber
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