Structural Effects of C6 Substitution in 6-(4-(Dimethylamino)phenyl)fulvenes

Autor:	and Donald V. Scaltrito, Matthew L. Peterson, Stuart W. Staley, Carl A. Morales, Jeffrey T. Strnad, Thomas P. Markotan
Rok vydání:	1999
Předmět:	chemistry.chemical_compound Crystallography Dipole chemistry Computational chemistry Aryl Organic Chemistry Space group Coplanarity Crystal structure Resonance (chemistry) Fulvene Natural bond orbital
Zdroj:	The Journal of Organic Chemistry. 64:9067-9076
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo990931x
Popis:	The single-crystal X-ray structures of 6-(4-(dimethylamino)phenyl)-6-methylfulvene (2) and of two polymorphs of 6-(4-(dimethylamino)phenyl)-6-phenylfulvene (3(P21/c) and 3(Pca21)) have been determined and the structures of a series of 6-arylfulvenes (1−8) have been optimized at the HF/6-31G level. Analysis of these structures reveals how resonance and crystal lattice effects influence the degree of coplanarity between the aryl and fulvene rings. The torsional angles at the aryl−fulvene bonds are significantly larger in the optimized structures than in the X-ray structures. Natural bond orbital π charges and dipole moments calculated for the X-ray and optimized structures show that the crystalline environment enhances molecular polarization. Qualitative responses for second harmonic generation in powder samples have been observed in 2, 3(Pca21), and 5. Compounds 2 and 3(Pca21) have similar packing motifs despite packing in different space groups.
Databáze:	OpenAIRE
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