The microwave spectrum and structure of fulvene

Baron, Paul A.; Brown, R. D.; Burden, Frank R.; Domaille, PJ; Kent, J. E.

doi:10.1016/0022-2852(72)90051-3

Cited by 106 publications

(59 citation statements)

References 20 publications

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“…Its dipole moment in the gas phase (0.42 D; 1 D= 3.33564 x 10-3° C m) (Baron, Brown, Burden, Domaille & Kent, 1972) is essentially identical to that of cyclopentadiene (Scharpen & Laurie, 1965 A high level of electron correlation is required in order to reproduce the fulvene value theoretically (Replogle, Trucks & Staley, 1991). There is ample evidence that fulvene and 6-arylsubstituted fulvenes are quite polarizable.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure and crystal packing of 6-(p-dimethylaminophenyl)fulvene

Wingert¹,

Staley²

1992

Acta Crystallogr Sect B

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The single-crystal structure of 6-(p-dimethylaminophenyl)fulvene (DMAPF), ClaHlsN, Mr = 197.28, F(000) = 848, at 123 K has been determined and refined from Mo Ka (A = 0.7107 ,~) X-ray data collected up to sin0/a = 0. (13) A 3. The structure was refined using 6459 unique reflections to a final wR of 5.89% with anisotropic temperature factors on non-H atoms, isotropic temperature factors on H atoms, and populations of radial electron density distributions on every atom as variables in the refinement. All reflections were treated as observed. In both molecules of the asymmetric unit the dihedral angle between the benzenoid and fulvene rings is approximately 15 °, whereas pyramidalization at the N atom is 2.5 times greater in one molecule than in the other. The crystal structure is composed of layers parallel to the ab plane with molecules aligned in the c direction. The molecules of each layer pack with their cross-sections forming a herringbone pattern. Comparison of geometric and electronic features of crystalline DMAPF with those derived by molecular orbital calculations indicate enhanced polarization due to the crystal field.

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Section: Introductionmentioning

confidence: 99%

Molecular structure and crystal packing of 6-(p-dimethylaminophenyl)fulvene

Wingert¹,

Staley²

1992

Acta Crystallogr Sect B

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“…The positive value of dipole moment (for R=NO 2 , CN, NC, Cl) indicates that the electron density in the region of space surrounding the C10=R 2 or C10-(C 6 H 4 -R) 2 group is larger than that in the region surrounding C 5 H 4 fivemembered ring. Therefore, the electric charge of the latter is positive, while that of the first region is negative.…”

Section: Dipole Momentsmentioning

confidence: 99%

“…Fulvene has been shown by spectroscopic methods to be a planar, non-aromatic molecule of C 2v symmetry with C-C bonds that alternate in length, consistent with localized single and double bonds [1,2]. The fulvene properties, as well as properties of its derivatives (fulvenes), have been the subject of numerous experimental [2][3][4][5] and theoretical investigations [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]. Further, the methods for generation of fulvenes and their rich cycloaddition chemistry have been recently reviewed [3].…”

Section: Introductionmentioning

confidence: 99%

Electronic properties and aromaticity of substituted diphenylfulvenes in the ground (S0) and excited (T1) states

Sadlej-Sosnowska

2017

Struct Chem

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In the present account, we investigate electronic properties of diphenylfulvene and its derivatives substituted in phenyl rings. The results were compared with the analogous properties of fulvene and its derivatives with the same substituents at the exocyclic carbon atom. All properties were evaluated and compared in the ground electronic S 0 state and in the first excited T 1 triplet state. These properties are dipole moments, charges, number of π electrons, and aromaticity of the fulvenic, five-membered ring in the two sets of compounds. The latter property was estimated by the harmonic oscillator model for aromaticity (HOMA) index and, for the fulvenes group, by the calculation of aromatic stabilization energy in both electronic states. It was also investigated whether Baird's rule alone can account for the aromaticity differences in the two electronic states.

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“…The bond distances in the fulvene moiety have the characteristics of a non-aromatic butadiene-type structure with alternate double and single C(spE)-C(sp 2) bond values as seen in pentafulvene (Baron, Brown, Burden, Domaille & Kent, 1972), 6-6 dimethylpentafulvene (Chiang & Bauer, 1970) and octachloropentafulvene (Ammon, Wheeler & Agranat, 1973). The three single bonds C(5)-C(9)= 1.456 (2), C(6)-C(7) = 1.456 (2) and C(7)-C(8)= 1.462 (2)/~ are all slightly shorter than the 'pure' C(sp2)-C(sp 2) single bond, 1.485 A (Dewar & Schmeising, 1960), and the three double bonds C(5)-C(6)= 1.379 (2), C(8)-C(9)= 1.354(2) and C(7)-C(15)= 1.359(2)A are all a little longer than the C(sp2)-C (sp 2) double bond as in ethylene, 1.337 A (Bartell, Roth, Hollowell, Kuchitsu & Young, 1965).…”

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confidence: 99%