Abstract
Organic chemistry is a broad field which includes activities that intersect with such diverse areas as biology, medicine and pharmacology, materials science, chemical and petroleum engineering, and fundamental studies of molecular structure. The purpose of this text is to provide coverage of a central core of organic chemistry. This core of knowledge can be applied within organic chemistry or to other fields, such as those named above, which require significant contributions from organic chemistry. One organizational approach to organic chemistry divides it into three main areas. These areas are structure, dynamics, and synthesis. Structure includes the description of organic molecules and the methods for determining, analyzing, and predicting molecular geometry and bonding. Dynamics refers to the chemical and physical properties and transformations of molecules. Synthesis includes those activities which permit chemists to assemble new molecules and to convert existing substances into new compounds. These three areas are all interrelated, but synthesis is built on knowledge of both structure and reactions (chemical dynamics), while understanding dynamic processes ultimately rests on detailed knowledge about molecular structure. A firm grounding in the principles of structure and chemical bonding is therefore an essential starting point for fuller appreciation of dynamics and synthesis. In this first chapter we will discuss the ideas that have proven most useful to organic chemists for describing and correlating facts, concepts, and theories about the structure of organic molecules.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
General References
C. K. Ingold, Structure and Mechanism in Organic Chemistry, Second Edition, Cornell University Press, Ithaca, New York, 1969.
L. N. Ferguson, Organic Molecular Structure, Willard Grant Press, Boston, 1975.
A. Streitwieser, Jr., Molecular Orbital Theory for Organic Chemists, John Wiley and Sons, New York, 1961.
M. J. S. Dewar, The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill Book Co., New York, 1969.
K. B. Wiberg, Physical Organic Chemistry, John Wiley and Sons, New York, 1964.
A. Liberles, Introduction to Theoretical Organic Chemistry, Macmillan., New York, 1968.
R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970.
M. Orchin, The Importance of Antibonding Orbitals, Houghton Mifflin, Boston, 1967.
W. T. Borden, Modern Molecular Orbital Theory for Organic Chemists, Prentice-Hall, Englewood Cliffs, New Jersey, 1975.
H. E. Zimmerman, Quantum Mechanics for Organic Chemists, Academic Press, New York, 1975.
I. G. Cszimadia, Theory and Practice of MO Calculations on Organic Molecules, Elsevier, Amsterdam, 1976.
M. J. S. Dewar and R. C. Dougherty, The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975.
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976.
L. Salem, Electrons in Chemical Reactions, Wiley, New York, 1982.
Chapter 1
H. Prinzbach, Pure Appl. Chem. 28, 281 (1971).
E. S. Gould, Mechanism and Structure in Organic Chemistry, Holt—Dryden, New York, 1959, pp. 69, 70.
T. J. Barton, R. W. Roth, and J. G. Verkade, J. Am. Chem. Soc. 94, 8854 (1972).
R. L. Reeves and W. F. Smith, J. Am. Chem. Soc. 85, 724 (1963).
R. B. Martin, J. Chem. Soc. Chem. Commun. 793 (1972).
J. A. Joule and G. F. Smith, Heterocyclic Chemistry, Van Nostrand—Reinhold, London, 1972, pp. 194–195;
J. A. Joule and G. F. Smith, Heterocyclic Chemistry, Van Nostrand—Reinhold, London, 1972, p. 64.
H. L. Ammon and G. L. Wheeler, J. Am. Chem. Soc. 97, 2326 (1975).
R. Breslow, T. Eicher, A. Krebs, R. A. Peterson, and J. Posner, J. Am. Chem. Soc. 87, 1320 (1965).
R. B. Woodward, J. Am. Chem. Soc. 63, 1123 (1941) .
R. T. Sanderson, J. Am. Chem. Soc. 97, 1367 (1975).
D. W. Davis, D. A. Shirley, and T. D. Thomas, J. Am. Chem. Soc. 94, 6565 (1972).
R. C. Bingham, J. Am. Chem. Soc. 98, 535 (1976).
W. L. Jorgensen and L. Salem, The Organic Chemist’s Book of Orbitals, Academic Press, New York, 1973, pp. 179–184.
H. Stafast and H. Bock, Tetrahedron 32, 855 (1976).
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley—Interscience, New York, 1976, pp. 51–57.
L. Libit and R. Hoffmann, J. Am. Chem. Soc. 96, 1370 (1974).
W. J. Hehre, L. Radom, and J. A. Pople, J. Am. Chem. Soc. 94, 1496 (1972).
R. Breslow and J. M. Hoffmann, Jr., J. Am. Chem. Soc. 94, 2110 (1972).
R. Breslow and P. Dowd, J. Am. Chem. Soc. 85, 2729 (1963).
R. Breslow and W. Chu, J. Am. Chem. Soc. 95, 411 (1973).
W. L. Jorgensen and L. Salem, The Organic Chemist’s Book of Orbitals, Academic Press, 1973, pp. 93, 94.
R. Breslow and J. M. Hoffmann, J. Am. Chern. Soc. 94, 2110 (1972);
M. Saunders, R. Berger, A. Jaffe, M. McBride, J. O’Neill, R. Breslow, J. M. Hoffmann, C. Perchonock, E. Wasserman, R. S. Hutton, and V. J. Kuck, J. Am. Chem. Soc. 95, 3017 (1973);
R. Breslow and S. Mazur, J. Am. Chem. Soc. 95, 584 (1973).
C. A. Coulson and A. Streitwieser, Jr., Dictionary of π-Electron Calculations, W. H. Freeman and Co., San Francisco, 1965, p. 184.
R. E. Lehr and A. P. Marchand, Orbital Symmetry: A Problem-Solving Approach, Academic Press, New York, 1972, p. 37.
C. A. Coulson and A. Streitwieser, Jr., Dictionary of π-Electron Calculations, W. H. Freeman and Co., San Francisco, 1965, p. 1.
N. L. Allinger and N. A. Pamphilis, J. Org. Chem. 38, 316 (1973).
K. B. Wiberg and F. H. Walker, J. Am. Chem. Soc. 104, 5239 (1982).
R. B. Turner, B. J. Mallon, M. Tichy, W. v. E. Doering, W. R. Roth, and G. Schröder, J. Am. Chem. Soc. 95, 8605 (1973).
P. J. Krueger and J. Jan, Can. J. Chem. 48, 3236 (1970);
M. D. Rozeboom and K. N. Houk, J. Am. Chem. Soc. 104, 1189 (1982).
R. D. Bertrand, D. M. Grant, E. L. Allred, J. C. Hinshaw, and A. B. Strong, J. Am. Chem. Soc. 94, 997 (1972).
K. W. Cox, M. D. Harmony, G. Nelson, and K. B. Wiberg, J. Chem. Phys. 50, 1976 (1969)
K. N. Houk and L. L. Munchausen, J. Am. Chem. Soc. 98, 937 (1976).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1984 Springer Science+Business Media New York
About this chapter
Cite this chapter
Carey, F.A., Sundberg, R.J. (1984). Chemical Bonding and Molecular Structure. In: Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-1143-1_1
Download citation
DOI: https://doi.org/10.1007/978-1-4757-1143-1_1
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4757-1145-5
Online ISBN: 978-1-4757-1143-1
eBook Packages: Springer Book Archive