The structure of thiepin 1,1-dioxide

Ammon, Herman L.; Watts, Plato H.; Stewart, J. M.; Mock, William L.

doi:10.1021/ja01018a083

Cited by 29 publications

(8 citation statements)

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“…Recently, we reported the preparation of a remarkably stable simple thiepin system, thieno[3,4-</]thiepin (l).1 The chemical and spectroscopic behavior of 1 has been compared to the thiepin sulfoxide 2 and the thiepin sulfone 3.2 These studies have shown that thiepin 1 possesses considerable aromatic-like character relative to heterocycles 2 and 3.2 It has been suggested that the unique properties of 1 may be due to groundstate contribution from azulene-like charge-separated species such as 4.1 In order to ascertain the nature of the -electron delocalization in 1, an X-ray determination of the molecular geometry of the thiepin along with the thiepin sulfone 3 was undertaken. We now wish to report that thiepin 1 is a planar system which has a crystal structure remarkably similar to the hydrocarbon azulene, while thiepin 3 shows nonplanar geometry which resembles that found for other thiepin sulfones. 3 Thiepin 1 forms bright yellow plate-like crystals which are monoclinic, with a = 8.273, b = 6.105, and c = 7.754 A, and ß = 103°57'.…”

Section: Electrooxidation Of Benzenementioning

confidence: 79%

“…We now wish to report that thiepin 1 is a planar system which has a crystal structure remarkably similar to the hydrocarbon azulene, while thiepin 3 shows nonplanar geometry which resembles that found for other thiepin sulfones. 3 Thiepin 1 forms bright yellow plate-like crystals which are monoclinic, with a = 8.273, b = 6.105, and c = 7.754 A, and ß = 103°57'. Systematic absences of the type (hOl) l odd, and (O/cO) k odd, suggested the space group to be P2i/c.…”

Section: Electrooxidation Of Benzenementioning

confidence: 79%

See 1 more Smart Citation

Electrooxidation of benzene

Osa¹,

Yıldız²,

Kuwana³

1969

J. Am. Chem. Soc.

118

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Section: Electrooxidation Of Benzenementioning

confidence: 79%

Section: Electrooxidation Of Benzenementioning

confidence: 79%

Electrooxidation of benzene

Osa¹,

Yıldız²,

Kuwana³

1969

J. Am. Chem. Soc.

118

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“…The value is typical of the C-S distance in many aromatic sulfones (ref. 7 in Ammon, Watts, Stewart & Mock, 1968). An unexpected structural feature is revealed in the C=C lengths, average 1.311 A, which are shorter than the usual value of 1.34 A (Table 5 in Ammon et al, 1970;March, 1968).…”

Section: Discussionmentioning

confidence: 99%

The crystal structure of a sulfone, 4,5-dihydrothiepin 1,1-dioxide

Ammon¹,

Smith²,

Kelso³

1972

Acta Crystallogr Sect B

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4,5-Dihydrothiepin 1,1-dioxide, C6H8802, crystallizes in the monoclinic space group P21/n with cell dimensions of a= 11"415, b=6"476, c=9-597 A, fl= 108.02 °, and with Z=4. Three-dimensional X-ray intensity data were collected with Mo radiation using a Picker diffractometer. The structure was solved with direct methods. Full-matrix least-squares refinement, using anisotropic temperature factors for C, O, and S and isotropic terms for H, gave an R of 0"049 (weighted R = 0.039). The conformation of the 7-membered ring is not symmetrical. Although the C-S lengths are typical of many of the values reported for aromatic sulfones, the C=C distances are smaller than the usual 1.34 A ethylenic value. A possible rationale for this shortening is given.

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“…13 LCI-SCF-MO (PPP) Treatment. In the calculations, compound 8 was approximated as 4-hydroxy-4ff-borepino[3,2-6:6,7-6']dithiophene (10) and compound 9 as 4/i-borepino-[3,2-6:6,7-6'] dithiophene (7). The usual version of the PPP method was used.…”

Section: Methodsmentioning

confidence: 99%

Theoretical study of borepinodithiophenes

Jeffries¹,

Parkanyi²

1976

J. Phys. Chem.

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Borepinodithiophenes 287 ments, that there is an appreciable degree of bonding In a C-C "single" bond which separates two multiple bonds: K. Freí and H. J. Bernstein, J. Chem. Phys., 38, 1216(1963. ( 16) A similar Interpretation may be valid In the case of conjugation between double bonds. Thus, for example, while the C2-C3 distance in 1,3-butadiene Is somewhat less than a typical C-C single bond, 1.48 vs. 1.54 Á, the Ci-C2 and C3-C4 distances are almost exactly the same as the C=C bond length in ethylene, 1.336 vs. 1.337 Á, respectively: L. E.

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The structure of thiepin 1,1-dioxide

Cited by 29 publications

References 0 publications

Electrooxidation of benzene

Electrooxidation of benzene

The crystal structure of a sulfone, 4,5-dihydrothiepin 1,1-dioxide

Theoretical study of borepinodithiophenes

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