(E)-1-(3-Chlorophenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

Abstract

Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.005 Å; R factor = 0.059; wR factor = 0.185; data-to-parameter ratio = 14.1.The title zwitterion,, C 16 H 11 ClN 2 O, is approximately planar, the dihedral angle between the benzene ring and naphthalene ring system is 1.55 (13) ; an intramolecular N-HÁ Á ÁO hydrogen bond stabilizes the planar conformation. In the crystal, -stacking between the benzene ring and the naphthalene ring system of adjacent molecules links the molecules into supramolecular chains running along the b axis, the centroid-centroid distance being 3.765 (2) Å . Related literature

Tautomerization of diazene<=>hydrazine via single proton tautomerization, spectral, XRD/HSA-interactions, optical and DFT/TD-DFT of new hydrazine ligand

“…The molecule adopts zwitterionic form (i.e. proton from the hydroxyl in the naphthol group is transfer to the azo-group), the two groups are linked by an intramolecular N1-H1…O1 hydrogen bond, enclosing an S(6) ring motif [43,44]. The same hydrogen atom participates in a second intramolecular hydrogen bond N1-H1…O2 enclosing another S(6) ring motif (Fig.…”

A colloidal water-stable MOF as a broad-range fluorescent pH sensor via post-synthetic modification

“…S13, ESI †) which confers enhanced stability to the framework. 29,30 By comparison, PSM of UiO-66-NH 2 with acetic anhydride 24 at 80% conversion does not offer increased stability in base and the framework is totally disrupted under the same conditions. (Fig.…”

“…28 We reasoned that the incorporation of a resonant indole moiety into the framework structure via diazotization of the amino groups to obtain UiO-66-NQN-ind could potentially improve the UiO-66-NH 2 stability in basic media. 29,30 The PSM of UiO-66-NH 2 was carried out following a diazotization reaction (Scheme S1 and ESI †) 31 using 1-methylindole as a coupling agent to form UiO-66-NQN-ind. The bdc-NH 2 linkers were easily diazotized with NaNO 2 and HCl, and then reacted with the indol compound for 1 h to obtain UiO-66-NQN-ind 1h .…”

Crystal structure of a 1,1,2,2-tetrachloroethane-solvated hydrazinecarbothioamide compound

“…There is delocalized bonding throughout the O1-C1-C2-N7-N8-C9 chain, with bond dimensions very similar to those found in a series of 1-(2-phenyldiazen-2-ium-1-yl)-naphthalen-2-olate compounds studied by Benosmane et al (2013), Bougueria et al (2013a,b) and Chetioui et al (2013), showing a structure midway between the keto and phenolate forms of compound 3 in the Scheme; in particular, the C1-O1 bond length is 1.296 (5) Å and N7-N8 is 1.291 (5) Å .…”