ChemInform Abstract: Study of (1-Alkoxyethyl) Diphenylphosphine Oxides. Part 4. Conclusive Conformational Study by NMR and Molecular Mechanics Calculations

ChemInform ◽  
2010 ◽  
Vol 22 (28) ◽  
pp. no-no
Author(s):  
L. POGLIANI ◽  
D. VITERBO ◽  
M. GIANNINI ◽  
M. CERUTI ◽  
P. UGLIENGO
Keyword(s):  
Molecular Mechanics ◽  
Conformational Study ◽  
Molecular Mechanics Calculations

An X-ray and conformational study of the α-chloro derivatives of 5,7-dihydro-1,11-dimethyl-6H-dibenzo[a,c]cyclohepten-6-one

1994 ◽  
Vol 72 (6) ◽  
pp. 1481-1488
Author(s):  
Robert R. Fraser ◽  
Corinne Bensimon ◽  
Neil C. Faibish ◽  
Fanzuo Kong
Keyword(s):  
Molecular Mechanics ◽  
Benzene Ring ◽  
Membered Ring ◽  
Single Atom ◽  
Conformational Study ◽  
Molecular Mechanics Calculations ◽  
X Ray ◽  
Chloro Derivatives ◽  
Torsional Angles ◽  
Derivatives Of

The crystal structures for four α-chloro derivatives 2–5 of the titled ketone 1 have been determined, confirming their earlier assignments of stereochemistry. Variations in the conformations of 2–5 suggested some flexibility in the central seven-membered ring. Molecular mechanics calculations of the changes in energy as a function of the internal torsional angles at the carbonyl of these chloro derivatives indicated the ring flexibility to be comparable to that of cyclohexanone. In the three compounds containing an axial chlorine the distance between the chlorine atom and two of the carbon atoms of the more remote benzene ring was 3.2 ± 0.1 Å, suggesting the value for the thickness of a benzene ring may be significantly smaller than the accepted value when it is interacting with a single atom.

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