cis-2-Ethoxy-1-phenylsulfinylcyclopropane

Kimura, Masao; Ward, Mark A.; Watson, William H.; Venier, Clifford G.

doi:10.1107/s0567740879011626

Cited by 5 publications

(2 citation statements)

References 3 publications

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“…However, the molecular and crystal structure has been determined by electron [28,29] and X-ray diffraction [30 333] for certain related compounds containing an arylsulfinyl fragment, such as diphenyl sulfoxide [28,30], (+)-methyl p-tolyl sulfoxide [31], (+)-3-bis(phenylsulfinyl)methyl-1,2-dimethylcyclopropene [32], and cis-2-ethoxy-1-phenylsulfinylcyclopropane [33]. The following bond lengths (A) were reported: C sp 23S 1.804 (6) [28,29], 1.76 (2) [30], 1.797 (6) [31], 1.791(5), 1.802 (5) [32], and 1.77 (2) [33]; S=O 1.489(5) [28,29], 1.47 (2) [30], 1.493(6) [31], 1.508(4), 1.487(4) [32], and 1.509 (8) [33]. The C sp 23S=O bond angle (deg) was reported to be 106.1(0.4) [30], 106.5(0.3) [31], and 105.1(4) [33].…”

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confidence: 99%

“…The following bond lengths (A) were reported: C sp 23S 1.804 (6) [28,29], 1.76 (2) [30], 1.797 (6) [31], 1.791(5), 1.802 (5) [32], and 1.77 (2) [33]; S=O 1.489(5) [28,29], 1.47 (2) [30], 1.493(6) [31], 1.508(4), 1.487(4) [32], and 1.509 (8) [33]. The C sp 23S=O bond angle (deg) was reported to be 106.1(0.4) [30], 106.5(0.3) [31], and 105.1(4) [33]. As shown in [28333], the S=O groups are approximately coplanar to the phenyl rings to which they are bonded.…”

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confidence: 99%

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An ab initio Quantum-Chemical Study of C6H5S(O)CH3 and C6H5S(O)CF3

et al. 2005

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The potential functions of internal rotation around the C sp 23S bond in the C 6 H 5 S(O)CH 3 and C 6 H 5 S(O)CF 3 molecules were obtained by ab initio MP2(full)/6-31+G* calculations. The stationary points were identified by solving the vibrational problems. The structures in which the plane of the C sp 23S3C sp 3 bonds is approximately perpendicular to the benzene ring plane correspond to the energy minimum. The barriers to rotation around the C sp 23S bond, corrected for the zero-point vibration energy, are 21.29 [C 6 H 5 S(O)CH 3 ] and 28.98 [C 6 H 5 S(O)CF 3 ] kJ mol !1 . The bond angles (deg) are as follows: 95.7 (CSC), 107.1 (C sp 2SO), 106.3 (C sp 3SO) in C 6 H 5 S(O)CH 3 ; 93.5 (CSC), 108.2 (C sp 2SO), 105.2 (C sp 3SO) in C 6 H 5 S(O)CF 3 . The bond lengths are as follows (A): 1.520 (S=O), 1.804 (C sp 23S), 1.810 (C sp 33S) in C 6 H 5 S(O)CH 3 ; 1.507 (S=O), 1.799 (C sp 23S), 1.870 (C sp 33S) in C 6 H 5 S(O)CF 3 . According to the results of NBO calculations, the formally double S=O bond consists of a strongly polarized covalent s bond (S6O) and an almost ionic bond.An increase in the S=O bond multiplicity relative to a single bond is mainly due to hyperconjugation by the mechanism n(O)6s*(C sp 23S) and n(O)6s*(C sp 33S) and, to a lesser extent, by interaction of the oxygen lone electron pairs with the Rydberg orbitals of the S atoms, characterized by a large contribution of the d component.

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