Phenylhydrazine–borane adduct—characterized in the solid state and in solution

Wrackmeyer, Bernd; Giumanini, Angelo G.; Gambi, A.; Verardo, Giancarlo; Gilli, Gastone; Bertolasi, Valerio

doi:10.1002/hc.10049

Cited by 2 publications

(1 citation statement)

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“…Secondly, the C13-N31 bonds are short for their type [mean value (Allen et al, 1987) = 1.468 Å and lower quartile value = 1.460 Å ], while the N-O distances are all long for their type (mean value = 1.217 Å ); the marked difference between the N31-O31 and N31-O32 distances in compound (I) is noteworthy and is probably associated with the formation of the intramolecular N-HÁ Á ÁO hydrogen bond. Finally, the C14-N41 bond lengths are significantly less than that for the corresponding exocyclic bond [1.413 (5) Å ] in the 1:1 adduct of phenylhydrazine with borane [Cambridge Structural Database (CSD;Allen, 2002) refcode RUYJIE; Wrackmeyer et al, 2002]. These observations, which closely mimic those for the corresponding distances for 2-nitrophenylhydrazine in its 1:1 adduct with 1,3-dimethylbarbituric acid (CSD refcode QIGVEH; Bertolasi et al, 2001), provide evidence for some polarization of the electronic structure in compounds (I) and (II), with the polarized form (B) (see Scheme 2) making a significant contribution to the overall The molecular structure of compound (IV), showing the atom-labelling scheme.…”

Section: Commentmentioning

confidence: 99%

Four related esters: two 4-(aroylhydrazinyl)-3-nitrobenzoates and two 3-aryl-1,2,4-benzotriazine-6-carboxylates

et al. 2013

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The molecules of both methyl 4-[2-(4-chlorobenzoyl)hydrazinyl]-3-nitrobenzoate, C15H12ClN3O5, (I), and methyl 4-[2-(2-fluorobenzoyl)hydrazinyl]-3-nitrobenzoate, C15H12FN3O5, (II), contain an intramolecular N-H···O hydrogen bond, and both show electronic polarization in the nitrated aryl ring. In both compounds, molecules are linked by a combination of N-H···O and C-H···O hydrogen bonds to form sheets, which are built from R4(3)(18) rings in (I) and from R4(4)(28) rings in (II). In each of methyl 3-phenyl-1,2,4-benzotriazine-6-carboxylate, C15H11N3O2, (III), and methyl 3-(4-methylphenyl)-1,2,4-benzotriazine-6-carboxylate, C16H13N3O2, (IV), the benzotriazine unit shows naphthalene-type delocalization. There are no hydrogen bonds in the structures of compounds (III) and (IV), but in both compounds, the molecules are linked into chains by π-π stacking interactions involving the benzotriazine units. The mechanism of chain formation is the same in both (III) and (IV), and the different orientations of the two chains can be related to the approximate relationship between the unit-cell metrics for (III) and (IV).

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Section: Commentmentioning

confidence: 99%