Page 127 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

106 General References

CHAPTER 1
T. A. Albright, J. K. Burdett, and M. H. Whangbo, Orbital Interactions in Chemistry, John Wiley & Sons,
Chemical Bonding
and Molecular Structure New York, 1985.
R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Clarendon Press, Oxford, 1990.
W. T. Borden, Modern Molecular Orbital Theory for Organic Chemists, Prentice-Hall, Englewood Cliffs,
NY, 1975.
I. Fleming, Frontier Orbital and Organic Chemical Reactions, John Wiley & Sons, New York, 1976.
W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. Pople, Ab Initio Molecular Orbital Theory, Wiley-
Interscience, New York, 1986.
F. Jensen, Introduction to Computational Chemistry, John Wiley & Sons, Chichester, 1999.
W. Koch and M. C. Holthausen, A Chemist’s Guide to Density Functional Theory, Wiley-VCH, Chichester,
2000.
E. Lewars, Computational Chemistry, Kluwer Academic Publishers, Boston, 2003.
R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press,
Oxford, 1989.
L. Salem, Electrons in Chemical Reactions, John Wiley & Sons, New York, 1982.
P. v. R. Schleyer, ed., Encyclopedia of Computational Chemistry, John Wiley & Sons, New York, 1998.
H. E. Zimmerman, Quantum Mechanics for Organic Chemists, Academic Press, New York, 1975.

Problems

(References for these problems will be found on page 1155.)

1.1. Suggest an explanation for the following observations:
a. Although the hydrocarbon calicene has so far defied synthesis, but it has been
estimated that it would have a dipole moment as large as 5.6 D.

calicene
b. The measured dipole moment of 4-nitroaniline (6.2 D) is larger than the value
calculated using standard group dipoles (5.2 D).

H N NO 2
2
4-nitroaniline
c. The dipole moments of furan and pyrrole are in opposite directions.

O N
furan pyrrole
H
1.2. Predict the preferred site of protonation for each of the following molecules and
explain the basis of your prediction.
a. b. O c. d.
PhCH NPh CH 3 C N
N
NH 2 NH 2
H