%0 DATA
%A Tatyana, Voloshchuk
%A Nicola S., Farina
%A Orrette R., Wauchope
%A Magdalena, Kiprowska
%A Paul, Haberfield
%A Alexander, Greer
%D 2004
%T Molecular Bilateral Symmetry of Natural Products: Prediction of Selectivity of
Dimeric Molecules by Density Functional Theory and Semiempirical
Calculations
%U https://acs.figshare.com/articles/journal_contribution/Molecular_Bilateral_Symmetry_of_Natural_Products_Prediction_of_Selectivity_of_Dimeric_Molecules_by_Density_Functional_Theory_and_Semiempirical_Calculations/3331315
%R 10.1021/np049899e.s001
%2 https://acs.figshare.com/ndownloader/files/5170525
%K Density Functional Theory
%K bi
%K tetramer
%K symmetry
%K Molecular Bilateral Symmetry
%K calculation
%K C 2
%K trimer
%K Natural products 1
%K molecule
%K C 2 v point groups
%K sigma
%X A literature survey and theoretical calculations have been applied to explore bilateral symmetry in natural
product systems. Molecular bilateral symmetry is defined to include *C*_{2} (sigma plane or axis), *C*_{s}, and *C*_{2}_{v}
point groups in molecules. Natural products that possess chirality in the form of *C*_{2}-axes or sigma planes
of symmetry are present in higher proportions (69%) compared to molecules bearing achiral *C*_{s} or *C*_{2}_{v}
point groups (14% and 16%, respectively). Density functional theoretical and semiempirical calculations
indicate that the dimers 3,3‘-dibromo-5,5‘-[*N*-(2-(3-bromo-4-hydroxyphenyl)ethyl)-2-hydroxyiminoacetamide]biphenyl-2,2‘-diol (**1**), (*S*,*S*)-1,2-bis(2-amino-3*H*-imidazol-4-yl)-(*R*,*R*)-3,4-bis(1*H*-pyrrole-2-amido)cyclobutane (**2**), 2-oxo-dimethyl-1,3-bis(3,4-dibromobenzene-1,2-diol) (**11**), 1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (**12**), and bis(5-isopropyl-8-methylazulene)methane (**13**) evolve more
energy per connecting bond than the corresponding trimers or tetramers would. This we propose is a
guiding parameter that may adjust molecule growth. The corresponding trimers, tetramers, or higher
oligomers of **1**,** 2**, and **11**−**13 **appear to represent “missing” compounds in nature. Natural products **1**,** 2**,
and **11**−**13**, having 3-fold and higher levels of symmetry, would founder on the lack of a facile method of
synthesis and on the prohibitively high-energy costs caused by steric crowding at their core.