Comparison of conformer distributions in the crystalline state with conformational energies calculated by ab initio techniques.

Abstract:

:The conformational preferences of 12 molecular substructures in the crystalline state have been determined and compared with those predicted for relevant model compounds by ab initio molecular orbital calculations. Least-squares regression shows that there is a statistically significant correlation between the crystal-structure conformer distributions and the calculated potential-energy differences, even though the calculations relate to a gas-phase environment. Torsion angles associated with high strain energy (> 1 kcal mol-1) appear to be very unusual in crystal structures and, in general, high-energy conformers are underrepresented in crystal structures compared with a gas-phase, room-temperature Boltzmann distribution. It is concluded that crystal packing effects rarely have a strong systematic effect on molecular conformations. Therefore, the conformational distribution of a molecular substructure in a series of related crystal structures is likely to be a good guide to the corresponding gas-phase potential energy surface.

journal_name

J Comput Aided Mol Des

authors

Allen FH,Harris SE,Taylor R

doi

10.1007/BF00355046

subject

Has Abstract

pub_date

1996-06-01 00:00:00

pages

247-54

issue

3

eissn

0920-654X

issn

1573-4951

journal_volume

10

pub_type

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