Intramolecular sulphur(II)—oxygen interaction in sulphides and disulphides with 2-methoxycarbonylphenyl and 2-nitrophenyl groups: an X-ray study

Kucsman, Árpád; Kapovits, I.; Kövesdi, István; Kàlmán, Alajos; Pa̋rkányi, László

doi:10.1016/0022-2860(84)85031-0

Cited by 55 publications

(28 citation statements)

References 52 publications

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“…The conformations of the S-C bonds -coplanarity of the S-C(8) bonds with the respective Ph planes, orthogonality of the S-C(1) Ph bonds with the respective C 10 planes -comply with a pattern which is the predominant one in diaryl sulfides [23,27]. Even in "symmetrical" sulfides Ar 2 S the two S-C(1) Ar bonds behave differently.…”

Section: Di(8-phenylthio-naphth-1-yl) Disulfide (1a)mentioning

confidence: 78%

peri-Interactions in Naphthalenes, 12 [1]. The Significance of Linear and T-Shaped Arrangements in peri-Substituted Naphthalenes

Schiemenz

2004

Zeitschrift Für Naturforschung B

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Section: Di(8-phenylthio-naphth-1-yl) Disulfide (1a)mentioning

confidence: 78%

peri-Interactions in Naphthalenes, 12 [1]. The Significance of Linear and T-Shaped Arrangements in peri-Substituted Naphthalenes

Schiemenz

2004

Zeitschrift Für Naturforschung B

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“…Compound 3 is unusual in a few aspects. A search of the CSD shows that it is only the second example of a disulfide group appended by two phenyl rings [21] The first instance was reported by Kucsman and Kapovits and differs from the present compound in the length of the ester group [22]; being the methyl ester in comparison to the dodecyl equivalent presented herein. The dodecyl chain is also the longest benzoate ester reported in the CSD.…”

Section: X-ray Crystal Data Of Compoundmentioning

confidence: 99%

Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates

et al. 2017

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A series of dialkyl 2,2'-disulfanediyldibenzoates with alkyl chain length C8 to C12 were synthesized and characterized by spectral studies. The structure of compound 3 was also confirmed by X-ray crystallography. The compounds were found to possess good antibacterial activity, especially with respect to Gram positive bacteria, and the activity was found to increase with concomitant increase in chain length. Binding studies of compound 3 with the synthetic phospholipid 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) showed that the compound interacts with biological membrane mainly via hydrophobic interactions.

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“…12). In both 2,2 H -nitrodiphenyl sul®de (Kucsman et al, 1984) and 2,2 H ,4-trinitrodiphenyl sul®de (Aupers et al, 1999) only one of the nitro groups ortho to the S atom is approximately coplanar with its aryl ring. In the dinitro compound there are CÐHÁ Á ÁO…”

Section: Comparisons With Related Compoundsmentioning

confidence: 99%

“…Hence, when an electropositive atom X is placed ortho to the nitro group, it is to be expected that there will be an attractive electrostatic interaction between X and the neighbouring O atom. For example, when X is S, it is commonly observed that the shortest intramolecular SÁ Á ÁO distance is signi®cantly shorter than the sum of the van der Waals radii (Aupers et al, 1999;Kucsman et al, 1984;Kucsman & Kapovits, 1985).…”

Section: Introductionmentioning

confidence: 99%

Conformational preferences in 2-nitrophenylthiolates: interplay between intra- and intermolecular forces; structures of (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, S-(2-nitrophenyl)benzenecarbothiolate and 1-(2-nitrophenylthio)-2,5-pyrrolidinedione

Low

Storey

McCarron

et al. 2000

Acta Crystallogr Sect B

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In (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, C15H13NO2S (1) (orthorhombic Pbca), the nitro group is almost coplanar with the adjacent aryl ring, but the dihedral angles between the nitro-aryl and styryl fragments is approximately 121 degrees. The molecules are linked by paired C-H...O hydrogen bonds in a chain of rings. In S-(2-nitrophenyl)benzenecarbothiolate, C13H9NO3S (2) (monoclinic P2(1)/a), the nitro group is rotated by 33.0 (2) degrees out of the plane of the adjacent aryl ring and the thiobenzoate group is strongly twisted away from the plane of the disubstituted aryl ring. The molecules of (2) are linked into chains by C--H...O hydrogen bonds, and each chain is linked to two neighbouring chains by means of aromatic pi... pi stacking interactions. In 1-(2-nitrophenylthio)-2,5-pyrrolidinedione, C10H8N2O4S (3) (monoclinic P2(1)/a), the nitro group is again almost coplanar with the adjacent aryl ring, but the pyrrolidinedione unit is almost orthogonal to the O2NC6H4SN plane. There are three types of C-H...O hydrogen bond in the structure, and these link the molecules into a two-dimensional net. The conformations of these molecules have been investigated by SCF calculations and two energy minima have been identified for each: the molecules of (1) and (3) adopt conformations in their crystals which are close to those at the overall energy minima calculated for isolated molecules, while molecules of (2) adopt a conformation in the crystal close to that calculated for the local energy minimum. Comparisons are made with the structures of some related compounds and it is concluded that, while the nature of the two conformational minima is determined by intramolecular forces, the choice between them is determined primarily by intermolecular forces.

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Intramolecular sulphur(II)—oxygen interaction in sulphides and disulphides with 2-methoxycarbonylphenyl and 2-nitrophenyl groups: an X-ray study

Cited by 55 publications

References 52 publications

peri-Interactions in Naphthalenes, 12 [1]. The Significance of Linear and T-Shaped Arrangements in peri-Substituted Naphthalenes

peri-Interactions in Naphthalenes, 12 [1]. The Significance of Linear and T-Shaped Arrangements in peri-Substituted Naphthalenes

Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates

Conformational preferences in 2-nitrophenylthiolates: interplay between intra- and intermolecular forces; structures of (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, S-(2-nitrophenyl)benzenecarbothiolate and 1-(2-nitrophenylthio)-2,5-pyrrolidinedione

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