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journal article Mar 01, 1999

Conformational Studies in the Cyclohexane Series. 1. Experimental and Computational Investigation of Methyl, Ethyl, Isopropyl, andtert-Butylcyclohexanes

Kenneth B. Wiberg Jack D. Hammer Henry Castejon William F. Bailey Eric L. DeLeon Ronald M. Jarret
The Journal of Organic Chemistry Vol. 64 No. 6 pp. 2085-2095 · American Chemical Society (ACS)
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References
43
[1]
Barton D. H. R. Experientia (1950) 10.1007/bf02170915
[2]
Eliel E. L. (1965)
[3]
Eliel, E. L.; Wilen, S. H.Stereochemistry of Organic Compounds; Wiley:  New York, 1994; pp 665−834 and references therein.
[4]
Juaristi E. (1995)
[5]
Winstein S. J. Am. Chem. Soc. (1955) 10.1021/ja01626a037
[6]
Hirsch J. A. Top. Stereochem. (1967) 10.1002/9780470147108.ch4
[7]
Jensen F. R. Adv. Alicycl. Chem. (1971) 10.1016/b978-0-12-001303-6.50008-2
[8]
Bushweller C. (1995)
[9]
(a) Previous ab initio studies of monosubstituted cyclohexanes have been reviewed and the difficulties attending such calculations have been discussed; see:  Cremer, D.; Szabo, K. J. InConformational Behavior ofSix-Membered Rings; Juaristi, E., Ed.; VCH Publishers:  New York, 1995; pp 59−135.
[10]
Salzner U. J. Org. Chem. (1994) 10.1021/jo00087a035
[11]
Eliel E. L. J. Org. Chem. (1976) 10.1021/jo00886a026
[12]
Eliel E. L. J. Org. Chem. (1981) 10.1021/jo00322a056
[13]
Booth H. J. Chem. Soc., Perkin Trans. 2 (1980) 10.1039/p29800000255
[14]
The J. Am. Chem. Soc. (1971) 10.1021/ja00730a048
[15]
Subbotin J. Chem. Soc., Chem. Commun. (1976) 10.1039/c39760000141
[16]
Eliel J. Res. Natl. Bur. Stand. (1947)
[17]
Sergeyev N. M. Org. Magn. Reson. (1978) 10.1002/mrc.1270110306
[18]
(a) Slichter, C. P.Principles of Magnetic Resonance, 3rd ed.; Springer-Verlag:  Berlin, 1992; pp 254−64.
[19]
(b) Harris, R. K.NuclearMagnetic Resonance Spectroscopy; Wiley:  New York, 1986; pp 108−111.
[20]
Binsch G. Top. Stereochem. (1968) 10.1002/9780470147122.ch2
[21]
Ammann C. J. Magn. Reson. (1982)
[22]
Van Geet A. L. Anal. Chem. (1970) 10.1021/ac60288a022
[23]
Schneider H.-J. J. Am. Chem. Soc. (1976) 10.1021/ja00418a025
[24]
Siehl H.-U. J. Am. Chem. Soc. (1995) 10.1021/ja00127a011
[25]
Kates M. R. Ph.D. (1978)
[26]
An Algorithm for Least-Squares Estimation of Nonlinear Parameters

Donald W. Marquardt

Journal of the Society for Industrial and Applied... 1963 10.1137/0111030
[27]
Karpfen A. J. Phys. Chem. A (1997) 10.1021/jp971606l
[28]
Curtiss L. A. J. Chem. Phys. (1991) 10.1063/1.460205
[29]
Murcko M. A. J. Phys. Chem. (1996) 10.1021/jp9621742
[30]
Wiberg K. B. J. Am. Chem. Soc. (1988)
[31]
Microwave spectra of isotopic species and substitution structure of cyclohexane

J. Dommen, T. Brupbacher, G. Grassi et al.

Journal of the American Chemical Society 1990 10.1021/ja00159a007
[32]
Pedley J. B. (1994)
[33]
The B3LYP/6-311G* energies forn-pentane and neopentane are −197.813 79 and −197.815 34 H, respectively, giving a calculated energy difference of only 0.97 kcal/mol, or after correction for the difference in zero-point energy, 1.6 kcal/mol at 0 K. The experimental energy difference (ref 31) is 3.4 kcal/mol at 0 K.
[34]
Laidig K. E. J. Phys. Chem. (1991) 10.1021/j100173a029
[35]
Bartell L. S. J. Mol. Struct. (1976) 10.1016/0022-2860(76)85015-6
[36]
Heinrich F. Chem Ber. (1977) 10.1002/cber.19771100407
[37]
(c) For a concise discussion of the conformational analysis of 2,3-dimethylbutane and related molecules, see ref 4, p 605−606 and references therein.
[38]
Manoharan M. Tetrahedron Lett. (1984) 10.1016/s0040-4039(01)81359-9
[39]
Allinger N. L. J. Am. Chem. Soc. (1968) 10.1021/ja01007a017
[40]
van de Graaf B. Rec. Trav. Chim. Pays-Bas (1974) 10.1002/recl.19740930506
[41]
Adams R. J. Am. Chem. Soc. (1928) 10.1021/ja01394a026
[42]
Frisch M. J. (1995)
[43]
Cf (1958)
Cited By
126
The anomeric effect in substituted cyclohexanes. II. The role of hyperconjugative interactions and steric effect in 1,4-disubstituted cyclohexanes

Ferdinando Taddei, Erich Kleinpeter · 2005

Journal of Molecular Structure: THE...
Metrics
126
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43
References
Details
Published
Mar 01, 1999
Vol/Issue
64(6)
Pages
2085-2095
Authors
K
Kenneth B. Wiberg

Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, and Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610

J
Jack D. Hammer

Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, and Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610

H
Henry Castejon

Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, and Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610

W
William F. Bailey

Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, and Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610

E
Eric L. DeLeon

Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, and Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610

R
Ronald M. Jarret

Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, and Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610

Cite This Article
Kenneth B. Wiberg, Jack D. Hammer, Henry Castejon, et al. (1999). Conformational Studies in the Cyclohexane Series. 1. Experimental and Computational Investigation of Methyl, Ethyl, Isopropyl, andtert-Butylcyclohexanes. The Journal of Organic Chemistry, 64(6), 2085-2095. https://doi.org/10.1021/jo990056f
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