Structure of N-[bis(methylthio)methylene]cinnamamide, C12H13NOS2

Abstract

Abstract. M r = 251.34, monoclinic, P21/n, a =

Structural characterization and synthesis of 7-thia-1,5-diazatricyclo[7.4.1.05,14]tetradec-9(14)-ene-6,8-dithione

“…Both rings (3) and (3'), including the two terminal S atoms, are quite planar, with only the upper part of the ring, fused to the upper bieyclic system [(1) and (2) It is of interest to note the short non-bonded intramolecular contacts between the terminal S atoms and the ring S atoms ((S...S))=2.862/k. Similar types of non-bonded interactions involving S atoms have recently been observed in C12HlaNOS2 (Kamath & Venkatesan, 1984) and C12HIsC1NO2 S (Sergeyeva, Struchkov, Kurkutova, Zemlyanukhina, Sadovaya & Zefirov, 1984), where short S...O distances have been observed. This S...S interaction may be in part the result of intramolecular steric interactions between the terminal S atoms and the H atoms of the rings opposite them (Ym6n, 1983).…”

Structures and quantum-mechanical calculations of two polarized nitroethylenes: C9H9ClN2O2S (I) and C6H13N3O2 (II)

“…H31C31V"~ --(~ H2 1C3) 1974) or 1.409(4)A for 3-[bis(dimethylamino)-methylene]-3-phenyl-2-propanone (Kamath & Venkatesan, 1984). Moreover, the C-N bonds are significantly shortened: for the aminic nitrogens we found 1.335(4)A for C(2)-N(2) in (I) and 1.342 (4) A for C(2)-N(2) (cis to the nitro group) and 1.350 (4) A for C(2)-N(3) in (II).…”

A polarized, twisted, ethylene: structure of 3,3-bis(methylthio)-2-nitro-2-propene-1-nitrile, C5H6N2O2S2

“…(1)- (6) 179.8 (bromine-free analogue), 80.2, 55.4, 41.2, 39.9, 39.9 kJ mol -~ (for the bromine-free 1,3-dibenzyl analogue)] in Sandstr6m (1983) and references therein. X-ray data: (1) 2-p-bromobenzoyl-3,3-bis(methylthio)-2-propene-1-nitrile, 1.369 (7) (Abrahamsson, Rehnberg, Liljefors & Sandstr6m, 1974); (2) 3,3-bis(methylthio)-2-nitro-2-propene-1-nitrile, 1.376 (4) (present work); (3)[dimethylamino(methylthio)methylene]malononitrile, 1.397 (8) (Adhikesavalu & Venkatesan, 1983a); (4) 3-[bis (dimethylamino)methylene]-3-phenyl-2-propanone, 1.409 (4) (Kamath & Venkatesan, 1984); (5) 3-(1,3-dimethyl-2-imidazolidinylidene)-2-phenyl-2-propene-l-nitrile, 1.415 (8) (Kamath & Venkatesan, 1983, unpublished Final R = 0.064 for 8316 unique significant reflections. This is the first structural report of both molecules.…”

“…Push-pull substituents on ethylene considerably lower the free energy of activation (AG ~) to rotation around the double bond to below 105 kJ mo1-1. In the case of methyl 2-[bis(dimethylamino)methylene]-3-oxobutyrate trihydrate (Kamath & Venkatesan, 1984) [/(C=C) = 1.461 (4)/~], the AG* value is less than 33.6 kJ mol -~ (Sandstr6m, 1983).…”

“…Introduction. The purpose of the present investigation on the polarized ethylenes (Kamath & Venkatesan, 1984;Adhikesavalu & Venkatesan, 1981, 1983a is twofold: first, to study the molecular geometry of push-pull ethylenes with different donor and acceptor substituents, secondly, to look for any possible correlation that may be present between the C=C bond lengths and the rotational barrier about the ethylene bond for this class of molecules. The results are presented in this paper.…”