Metal-mediated cyanamide–hydroxyguanidine coupling

M.Y. Demakova, D.S. Bolotin, N.A. Bokach, G.L. Starova, V.Y. Kukushkin

Research output

13 Citations (Scopus)

Abstract

Reaction of the cyanamides R2NCN (R = Me 2a, Et 2b) with the hydroxyguanidine OC4H8NC(=NOH)NH2 (1) in the presence of zinc halides leads to [ZnX2{HN=C(NR2)ON=C(NH2)NC4H8O}] derived from the ZnII-mediated cyanamide–hydroxyguanidine coupling. This reaction is the first observation of interplay between any nitrile group and any hydroxyguanidine both in metal-involving and metal-free chemistry. Complexes 3a,b–5a,b rather rapidly degrade in solutions at RT, but solvates 3a,b•MeOH and 4a•MeOH are sufficiently stable in the solid state and they were characterized by IR, HRESI+-MS, solid state CP-MAS TOSS 13C NMR, and X-ray crystallography (for 3a,b). Complexes 4b and 5a,b were identified in solutions by HRESI+-MS.
Original languageEnglish
Pages (from-to)114-117
JournalInorganica Chimica Acta
Volume425
DOIs
Publication statusPublished - 2014

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Metals
Cyanamide
cyanamides
solid state
Nitriles
X ray crystallography
nitriles
metals
crystallography
halides
Zinc
zinc
Nuclear magnetic resonance
chemistry
nuclear magnetic resonance
x rays
hydroxyguanidine

Cite this

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title = "Metal-mediated cyanamide–hydroxyguanidine coupling",
abstract = "Reaction of the cyanamides R2NCN (R = Me 2a, Et 2b) with the hydroxyguanidine OC4H8NC(=NOH)NH2 (1) in the presence of zinc halides leads to [ZnX2{HN=C(NR2)ON=C(NH2)NC4H8O}] derived from the ZnII-mediated cyanamide–hydroxyguanidine coupling. This reaction is the first observation of interplay between any nitrile group and any hydroxyguanidine both in metal-involving and metal-free chemistry. Complexes 3a,b–5a,b rather rapidly degrade in solutions at RT, but solvates 3a,b•MeOH and 4a•MeOH are sufficiently stable in the solid state and they were characterized by IR, HRESI+-MS, solid state CP-MAS TOSS 13C NMR, and X-ray crystallography (for 3a,b). Complexes 4b and 5a,b were identified in solutions by HRESI+-MS.",
author = "M.Y. Demakova and D.S. Bolotin and N.A. Bokach and G.L. Starova and V.Y. Kukushkin",
year = "2014",
doi = "10.1016/j.ica.2014.10.015",
language = "English",
volume = "425",
pages = "114--117",
journal = "Inorganica Chimica Acta",
issn = "0020-1693",
publisher = "Elsevier",

}

TY - JOUR

T1 - Metal-mediated cyanamide–hydroxyguanidine coupling

AU - Demakova, M.Y.

AU - Bolotin, D.S.

AU - Bokach, N.A.

AU - Starova, G.L.

AU - Kukushkin, V.Y.

PY - 2014

Y1 - 2014

N2 - Reaction of the cyanamides R2NCN (R = Me 2a, Et 2b) with the hydroxyguanidine OC4H8NC(=NOH)NH2 (1) in the presence of zinc halides leads to [ZnX2{HN=C(NR2)ON=C(NH2)NC4H8O}] derived from the ZnII-mediated cyanamide–hydroxyguanidine coupling. This reaction is the first observation of interplay between any nitrile group and any hydroxyguanidine both in metal-involving and metal-free chemistry. Complexes 3a,b–5a,b rather rapidly degrade in solutions at RT, but solvates 3a,b•MeOH and 4a•MeOH are sufficiently stable in the solid state and they were characterized by IR, HRESI+-MS, solid state CP-MAS TOSS 13C NMR, and X-ray crystallography (for 3a,b). Complexes 4b and 5a,b were identified in solutions by HRESI+-MS.

AB - Reaction of the cyanamides R2NCN (R = Me 2a, Et 2b) with the hydroxyguanidine OC4H8NC(=NOH)NH2 (1) in the presence of zinc halides leads to [ZnX2{HN=C(NR2)ON=C(NH2)NC4H8O}] derived from the ZnII-mediated cyanamide–hydroxyguanidine coupling. This reaction is the first observation of interplay between any nitrile group and any hydroxyguanidine both in metal-involving and metal-free chemistry. Complexes 3a,b–5a,b rather rapidly degrade in solutions at RT, but solvates 3a,b•MeOH and 4a•MeOH are sufficiently stable in the solid state and they were characterized by IR, HRESI+-MS, solid state CP-MAS TOSS 13C NMR, and X-ray crystallography (for 3a,b). Complexes 4b and 5a,b were identified in solutions by HRESI+-MS.

U2 - 10.1016/j.ica.2014.10.015

DO - 10.1016/j.ica.2014.10.015

M3 - Article

VL - 425

SP - 114

EP - 117

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

SN - 0020-1693

ER -