New bisphosphonium salt containing a 1,4-dihydroxynaphthalene moiety: molecular and supramolecular structure

Copper Complexes of 1,4-Naphthoquinone Containing Thiosemicarbazide and Triphenylphosphine Oxide Moieties; Synthesis and Identification by NMR, IR, Mass, UV Spectra, and DFT Calculations

“…Thiosemicarbazides 14a-f were prepared by reacting substituted isothiocyanates 13a-f with hydrazine in ethanol as a solvent. 23 Upon mixing equimolar amounts of 14a-f with 2,3dichloro-1,4-naphthoquinone (7), Ph 3 P, and in the presence of Et 3 N as a catalyst and acetonitrile as a solvent, triphenylphosphine-ylidene(-3,4-dihydronaphthalen-2(1H)-ylidene)-N-substituted-hydrazine-1-carbothioamides 15a-f were obtained in 72−82% yield (Scheme 3).…”

“…In the same manner, bisphosphonium salt containing a 1,4-dihydroxynaphthyl-substituted moiety was synthesized in high yield by the reaction of 2-methyl-1,4-naphthoquinone with three equivalents of Ph 3 P and hydrogen bromide. 7 Metal-free synthesis of aryltriphenylphosphonium bromides by the reaction of Ph 3 P with aryl bromides in refluxing phenol was developed. 8 With the high reactivity of naphthoquinones, 2,3-dichloro-1,4-naphthoquinone (DCHNQ, 7 ) reacted with nucleophiles and substituted one or both chlorine atoms.…”

“…3 The reactions of 1,4-naphthoquinone with triphenylphosphine (Ph 3 P) have been previously described. As, for example, in the reaction of fluoronaphthoquinone (1) with triphenyl-phosphine (Ph 3 P), derivatives of phosphonium betaines derived from hexafluoro-1,4-naphthoquinone: (triphenyl- [5,6,7,8-tetrafluoro-1-oxido-4-oxo-3-(phenylimino)-3,4-dihydro-naphthalen-2-yl]phosphonium) 3 (Scheme 1), were obtained. 4 The reaction was explained as due to the formation of intermediate 2 (Scheme 1).…”

“…Depending upon reaction conditions, it was reported that Ph 3 P reacted with p-chloranil (4) to produce either Zwitter salts 5 or 6 5 (Scheme 1). However, in aqueous alcoholic medium, 3-(triphenylphosphoranylidene)naphthalene-1,2,4(3H)-trione (8) 6 was obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone (7) with Ph 3 P (Scheme 1).…”

“…For example, 4-cyclohexyl-3-(4-nitrophenyl)methyl-1,2,4-triazolin-5-thione has no activity against some selected bacteria, but after obtaining the metal(II) complex, the activity increases to a mild score. 22 From this, we here aim to investigate the reaction of 2,3dichloro-1,4-naphthoquinone (7) together with thiosemicarbazides and Ph 3 P to achieve the expected bi-nucleophilic substituted naphthoquinone. The newly obtained triphenylphosphine-ylidene-3,4-dihydronaphthalen-2(1H)-ylidene)-Nsubstituted-hydrazine-1-carbothioamides were then subjected to complexation toward CuCl 2 and Ph 3 P. The stability of these complexes was discussed using a plethora of quantum mechanical calculations and by executing Hirshfeld surface (HS) analysis.…”