Abstract
The subject paper presented the first conformational analysis of the anomeric effect within the context of molecular orbital theory, discussed the utility of Fourier decomposition of a torsional coordinate as a method for analyzing disparate electronic influences on that coordinate, and helped settle debate on the nature of anomeric stabilization.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Jeffrey GA, Pople JA, Radom L (1972) Carbohydr Res 25: 117
Jungius CL (1905) Z Phys Chem 52: 97
Lemieux RU (1964) In: de Mayo P (ed) Molecular rearrangements. Interscience, New York, p 709
Pearson CG, Rumquist O (1968) J Org Chem 33: 2572
Kirby AJ (1983) The anomeric effect and related stereoelectronic effects at oxygen. Springer, Berlin Heidelberg New York
Thatcher GRJ (ed) (1993) The anomeric effect and associated stereoelectronic effects. American Chemical Society, Washington, D.C
Graczyk PP, Mikolajczyk M (1994) In: Eliel EL, Wilen SH (eds) Topics in stereochemistry. Wiley, New York, p 159
Angyal Si (1968) Aust J Chem 21: 2737
Eliel EL, Wilen SH (1994) Stereochemistry of organic compounds. Wiley, New York
Cramer CJ (1996) J Mol Struct (Theochem) 370: 135
Edward JT (1955) Chem Ind 1102
Anderson CB, Sepp DT (1967) J Org Chem 32: 607
Romers C, Altona C, Buys HR, Havinga E (1969) Top Stereochem 4: 39
Stoddart JF (1971) Stereochemistry of carbohydrates. WileyInterscience, New York
Berman HM, Chu SSC, Jeffrey GA (1967) Science 157: 1576
Wolfe S, Rauk A, Tel LM, Czismadia IG (1971) J Chem Soc B 136
Radom L, Hehre WJ, Pople JA (1971) J Am Chem Soc 93: 289
Hehre WJ, Radom L, Schleyer PvR, Pople JA (1986) Ab initio molecular orbital theory. Wiley, New York
Radom L, Hehre WJ, Pople JA (1972) J Am Chem Soc 94: 2371
Tvaroska I, Bleha T (1975) Tetrahedron Lett 16: 249
Tvaroska I, Bleha T (1989) Adv Carbohydr Chem Biochem 47: 45
Wolfe S, Whangbo M-H, Mitchell DJ (1979) Carbohydr Res 69: I
Thogersen H, Lemieux RU, Bock K, Meyer B (1982) Can J Chem 60: 44
Cramer CJ (1992) J Org Chem 57: 7034
Cramer CJ, Truhlar DG (1993) J Am Chem Soc 115: 5745
Barrows SE, Dulles FJ, Cramer CJ, Truhlar DG, French AD (1995) Carbohydr Res 276: 219
Cramer CJ, Truhlar DG, French AD (1997) Carbohydr Res 298: 1
Barrows SE, Storer JW, Cramer CJ, French AD, Truhlar DG (1998) J Comput Chem 19: 1111
Cremer D, Pople JA (1975) J Am Chem Soc 97: 1354
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2000 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Cramer, C.J. (2000). Sugar anomerism — a short and sweet digression Perspective on “The application of ab initio molecular orbital theory to the anomeric effect”. In: Cramer, C.J., Truhlar, D.G. (eds) Theoretical Chemistry Accounts. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-10421-7_43
Download citation
DOI: https://doi.org/10.1007/978-3-662-10421-7_43
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-67867-0
Online ISBN: 978-3-662-10421-7
eBook Packages: Springer Book Archive