Roy, Tapta Kanchan ; Ghanta, Susanta ; Mondal, Tanmoy ; Saritha, Banda ; Mahapatra M., S. (2007) Conformational preferences of mono-substituted cyclohydronitrogens: a theoretical study Journal of Molecular Structure: Theochem, 822 (1-3). pp. 145-150. ISSN 0166-1280
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.theochem.2007.08.003
Abstract
The conformational stability of mono-substituted six membered cyclic hydronitrogens (N6H5X) are investigated with the aid of electronic structure calculations. One or both hydrogens adjacent to the substituent bearing nitrogen move to the equatorial position to attain the global minimum depending on the electronegativity of X. For example, strongly electronegative substituent like F pushes both the adjacent hydrogens into equatorial position, whereas covalent bond forming amino group prefers both the hydrogens to be in the axial position. When chlorine is the substituent, it migrates to the other end of the ring and forms hydrogen bonds with two of the axial hydrogen atoms in that region. Natural bond orbital analysis indicates that all these phenomena are a manifestation of the anomeric effect to different degrees.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Conformational Stability; Anomeric Effect; Natural Bond Orbital Analysis |
ID Code: | 79374 |
Deposited On: | 25 Jan 2012 13:13 |
Last Modified: | 22 Dec 2014 10:47 |
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