An X-ray crystallographic study of 1,2,5- and 1,3,5-triazapentadienium salts, C6H14N3+.ClO4−, C6H14N3+.ClO4−, C6H14N3+.C6H2N3O7−

Gould, Robert O.; McNab, Hamish; Walkinshaw, Malcolm D.

doi:10.1107/s0108270183007520

Cited by 3 publications

(4 citation statements)

References 6 publications

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“…1 660 ,cm-' (CO); 6,7.7-6.9 (1 5 H, m); 6, 178.98 (q), 167.47 (q), and overlapping and 2.34 (3 H, s); 6,179.06 (q), 167.29 (q), 143.31 (q), 136.39 (q), overlapping benzenoid signals in the range 128-131, and 21.39; m/z 299 ( M + , 43%), 119 (loo), 91 (47), 77 (24), and 51 (11). These compounds were particularly prone to hydrolysis, and were normally stored at -20 "C.…”

Section: L-aryl-33-diphenyl-2-azaprop-2-en-1 -Onesmentioning

confidence: 99%

Thermolysis of polyazapentadienes. Part 11. Concerted and free radical mechanisms in 2-aza enone and 2-aza enthione pyrolyses: crystal and molecular structures of 3-dimethylamino-1-p-tolyl-2-azaprop-2-en-1-one and 3-dimethylamino-1-phenyl-2-azaprop-2-ene-1-thione

Blake¹,

McNab²,

Murray³

1989

J. Chem. Soc., Perkin Trans. 1

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Flash vacuum pyrolysis of the dimethylamino-azapropenones (7)-( 9) and -azapropenethione (1 2) gives nitriles and amides (or thioamide) in yields of ca. 30% by an electrocyclisation-ring cleavage mechanism. This is a minor pathway for the triarylazapropenones ( 14) and (15) for which homolytic cleavage of the C-N bond gives rise to the major products. The X-ray crystal structures of ( 10) and (I 2)show that the conjugated systems are almost planar in the s-Z conformation, as required for the electrocyclic ring closure.The work described in the previous paper explores the thermal cleavage of HCN from the central atoms of an azoalkene unit (1). The terminal nitrogen atom is apparently not necessary for this behaviour, since there is considerable evidence that 2-aza dienes (2) can decompose by a similar mechanism,2 and that other terminal hetero-atoms can also become involved e.g. (3).3 However, alternative free-radical cleavage may be observed, e.g. (4).' An extension of these ideas to 2-aza enones ( 5 ) and 2-aza enethiones (6) is now described, in which the interpretation of the pyrolysis results is reinforced by X-ray crystallographic studies of typical precursors.

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Section: L-aryl-33-diphenyl-2-azaprop-2-en-1 -Onesmentioning

confidence: 99%

Thermolysis of polyazapentadienes. Part 11. Concerted and free radical mechanisms in 2-aza enone and 2-aza enthione pyrolyses: crystal and molecular structures of 3-dimethylamino-1-p-tolyl-2-azaprop-2-en-1-one and 3-dimethylamino-1-phenyl-2-azaprop-2-ene-1-thione

Blake¹,

McNab²,

Murray³

1989

J. Chem. Soc., Perkin Trans. 1

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“…The corresponding 1,1,5,5-tetramethyl derivative, (2) (Gould, McNab & Walkinshaw, 1983), and the 1-aryl derivative, (3) (Nagel & Allmann, 1981), have been reported.…”

Section: Commentmentioning

confidence: 99%

“…In (2), the planes of the anions and cations are mutually perpendicular with the appropriate O atoms of the nitro groups in the picrate anion interacting with the N atoms of the triazapentadienium chain (Gould, McNab & Walkinshaw, 1983). In contrast, interionic contact in (1) is dominated by a hydrogen bond between H5 in the cation and O1' (the phenolic O atom) of the picrate: the O...H distance is 1.931 (5),~ c20 T…”

Section: Commentmentioning

confidence: 99%

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1,1-Dimethyl-5-phenyl-1,2,5-triazapentadienium picrate

Blake¹,

Gould²,

Irving³

et al. 1994

Acta Crystallogr C

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The structure determination of 1,1-dimethyl-5-phenyl-1,2,5-triazapentadienium picrate, C10H]aN~.C6H2N307-, illustrates the effects of two factors on the internal geometry of the 1,2,5-triazapentadienium system. The first is the presence at the 5 position of an aryl group, the second the existence of hydrogen bonding in the form of an N...O interionic contact of 2.784 (6)/~ between the cation and the phenolic O atom of the picrate anion. The triazapentadienium system is planar and the phenyl ring is twisted relative to it by only 1.4 °. Comparison is made with published structures containing the analogous cations with 1-aryl and 1,1,5,5-tetramethyl substituents.

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G

Buckingham¹

1990

Dictionary of Organic Compounds

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An X-ray crystallographic study of 1,2,5- and 1,3,5-triazapentadienium salts, C6H14N3+.ClO4−, C6H14N3+.ClO4−, C6H14N3+.C6H2N3O7−

Cited by 3 publications

References 6 publications

Thermolysis of polyazapentadienes. Part 11. Concerted and free radical mechanisms in 2-aza enone and 2-aza enthione pyrolyses: crystal and molecular structures of 3-dimethylamino-1-p-tolyl-2-azaprop-2-en-1-one and 3-dimethylamino-1-phenyl-2-azaprop-2-ene-1-thione

Thermolysis of polyazapentadienes. Part 11. Concerted and free radical mechanisms in 2-aza enone and 2-aza enthione pyrolyses: crystal and molecular structures of 3-dimethylamino-1-p-tolyl-2-azaprop-2-en-1-one and 3-dimethylamino-1-phenyl-2-azaprop-2-ene-1-thione

1,1-Dimethyl-5-phenyl-1,2,5-triazapentadienium picrate

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