Novel S–N ring contractions using the 4-phenyl-1,2,3,5-dithiadiazole dimer, the synthesis and X-ray crystal structures of [(PhCN2S2)2Cl][S3N3], [PhCN2S2][S3N3], and [PhCN2S2][S3N2]Cl, and an ab initio molecular-orbital study of the bonding in [PhCN2S2][S3N3]

Banister, Arthur J.; Hansford, Michael I.; Hauptman, Z.; Luke, Anthony W.; Wait, S. T.; Clegg, William; Jørgensen, Karl Anker

doi:10.1039/dt9900002793

Cited by 31 publications

(12 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The co-packing of monomers and dimers in (Ic) gives a rare opportunity to compare the molecular structures of dimerized and monomeric DTDA species that are chemically identical and that are under identical externally applied conditions. In particular, the mean S-S bond length in the DTDA ring has been a measure of interest (Banister et al, 1990). The singly occupied molecular orbital (SOMO) of the neutral DTDA radical is a * orbital delocalized over the S and N atoms of the heterocycle.…”

Section: Figurementioning

confidence: 99%

A third polymorph of 4-(2,6-difluorophenyl)-1,2,3,5-dithiadiazolyl

Fatila

Jennings²,

Goodreid

et al. 2010

Acta Crystallogr C Cryst Struct Commun

View full text Add to dashboard Cite

The crystal structure of a third polymorphic form of the known 4-(2,6-difluorophenyl)-1,2,3,5-dithiadiazolyl radical, C(7)H(3)F(2)N(2)S(2), is reported. This new polymorph represents a unique crystal-packing motif never before observed for 1,2,3,5-dithiadiazolyl (DTDA) radicals. In the two known polymorphic forms of the title compound, all of the molecules form cis-cofacial dimers, such that two molecules are pi-stacked with like atoms one on top of the other, a common arrangement for DTDA species. By contrast, the third polymorph, reported herein, contains two crystallographically unique molecules organized such that only 50% are dimerized, while the other 50% remain monomeric radicals. The dimerized molecules are arranged in the trans-antarafacial mode. This less common dimer motif for DTDA species is characterized by pi-pi interactions between the S atoms [S...S = 3.208 (1) A at 110 K], such that the two molecules of the dimer are related by a centre of inversion. The most remarkable aspect of this third polymorph is that the DTDA dimers are co-packed with monomers. The monomeric radicals are arranged in one-dimensional chains directed by close lateral intermolecular contacts between the two S atoms of one DTDA heterocycle and an N atom of a neighbouring coplanar DTDA heterocycle [S...N = 2.857 (2) and 3.147 (2) A at 110 K].

show abstract

Section: Figurementioning

confidence: 99%

A third polymorph of 4-(2,6-difluorophenyl)-1,2,3,5-dithiadiazolyl

Fatila

Jennings²,

Goodreid

et al. 2010

Acta Crystallogr C Cryst Struct Commun

View full text Add to dashboard Cite

show abstract

“…However one structure of S 3 N 2 +• AsF 6 − was claimed to be monomeric with the nearest S· · ·S contact of 4Å although no magnetic data for this salt were reported [107]. Banister and co-workers also published a structure in which S 3 N 2 +• and isoelectronic CNSSN • associated together through S S bonds with inter-molecular S· · ·S contacts of 2.8Å [109,110]. Various selenium analogs of 22, i.e.…”

Section: -Trithiadiazolium Radical Cationmentioning

confidence: 95%

RCNSSS+: A novel class of stable sulfur rich radical cations

Shuvaev

Passmore

2013

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…9 A co-crystal of PhCN 2 S 2 and S 3 N 3 involves an indeterminate degree of charge transfer (refcode SIHZAK). 10 The structure of 4-(3-fluoro-4-trifluoromethylphenyl)-1,2,3,5-dithiadiazolyl (refcode: UMAROP) is typical of a (distorted) cis-oid dimer, but is significant in the context of this work in that the lattice readily opens up to form channels when co-sublimed with N 2 , Ar, CO 2 or SO 2 (refcodes: UMARUV, UMASAC, UMASEG and UMASIK) to form hostguest gas-clathrates. 11 This is the only other case to our knowledge where co-crystallization with neutral molecules has previously been demonstrated in DTDA chemistry, although identification of electron density for the incorporated gas molecules relied on the delocalized solvent tools of the PLATON 'SQUEEZE' routine.…”

Section: Introductionmentioning

confidence: 99%