Sterically Crowded Heterocycles. XI. A Semiempirical Prediction of Enantiomerization Barriers for Substituted (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)-1-phenylprop-2-en-1-ones

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Title:Sterically Crowded Heterocycles. XI. A Semiempirical Prediction of Enantiomerization Barriers for Substituted (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)-1-phenylprop-2-en-1-ones
Creators:
Böhm, Stanislav
Pohl, Radek
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 11, pp. 1761-1769
Uncontrolled Keywords:Atropisomerism, Imidazo[1,2-<i>a</i>]pyridines, Rotation barriers, Semiempirical calculations, PM3 method, Transition states, Hindered rotation, Axial chirality

Abstract

Conformational behaviour and racemization paths of the parent skeleton are discussed using a threedimensional Φ,Ψ-energy map calculated by the semiempirical PM3 method. To restrain the number of possible racemization paths, a less sophisticated approach based on the PM3 heat of formation - torsion angle Φ relationships has been used for 5-substituted title molecules; the role of non-planar enantiomeric transition states is postulated. Plausibility of the simple theoretical procedure has been tested using two phenyl derivatives of the title compounds for which experimental barriers to racemization are accessible. <p>

Title:Sterically Crowded Heterocycles. XI. A Semiempirical Prediction of Enantiomerization Barriers for Substituted (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)-1-phenylprop-2-en-1-ones
Creators:
Böhm, Stanislav
Pohl, Radek
Kuthan, Josef
Uncontrolled Keywords:Atropisomerism, Imidazo[1,2-<i>a</i>]pyridines, Rotation barriers, Semiempirical calculations, PM3 method, Transition states, Hindered rotation, Axial chirality
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:11
Page Range:pp. 1761-1769
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991761UNSPECIFIED
ID Code:1593
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Böhm, Stanislav; Pohl, Radek; Kuthan, Josef (1999) Sterically Crowded Heterocycles. XI. A Semiempirical Prediction of Enantiomerization Barriers for Substituted (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)-1-phenylprop-2-en-1-ones. Collection of Czechoslovak Chemical Communications, 64 (11). pp. 1761-1769. ISSN 0010-0765

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