Synthesis and characterization of cyanohydroisocyanoborates. Reactivity of the isocyano group towards nucleophiles

Béla Gyôri, Z. Berente, István Lázár

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

AgCNBH2CN and AgCNBH(CN)2 were synthesized with AgCN in Me2S from Me2S·BH2CN and 4-cyanopyridine·BH(CN)2, respectively. These silver complexes were transformed into Na[BH2(CN)NC] and Na[BH(CN)2NC] salts. In these hydrolytically very stable borates the isocyano group proved to be the most reactive site. This observation was demonstrated by reactions with nucleophiles, namely H2S, NH4N3 and NH4SCN. In the first two cases isocyano group underwent transformation into -N(H)-C(H)=S and -1-(5H)tetrazolyl groups, respectively, which remarkably increase the stability of hydroborates towards acidic hydrolysis. Unlike alkyl- or arylisocyanides, isocyano groups here do not form ring in reaction with NH4SCN, but most probably transform into -N=C(H)-NCS groups. All compounds, including the E- and Z-isomers (where appropriate), were characterized by IR, 1H, 11B and 13C NMR spectroscopy.

Original languageEnglish
Pages (from-to)3175-3180
Number of pages6
JournalPolyhedron
Volume17
Issue number18
Publication statusPublished - Aug 31 1998

Fingerprint

Borates
Nucleophiles
nucleophiles
Silver
Isomers
Nuclear magnetic resonance spectroscopy
Hydrolysis
Catalytic Domain
Magnetic Resonance Spectroscopy
reactivity
Salts
synthesis
borates
hydrolysis
isomers
silver
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
salts
nuclear magnetic resonance

Keywords

  • Cyanohydroisocyanoborates
  • Cyanohydrotetrazolylborates
  • Cyanohydrothioformamidoborates
  • E
  • Multinuclear NMR
  • Z-isomerism

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Synthesis and characterization of cyanohydroisocyanoborates. Reactivity of the isocyano group towards nucleophiles. / Gyôri, Béla; Berente, Z.; Lázár, István.

In: Polyhedron, Vol. 17, No. 18, 31.08.1998, p. 3175-3180.

Research output: Contribution to journalArticle

@article{39d7bb99c9814f76933649b7db06b017,
title = "Synthesis and characterization of cyanohydroisocyanoborates. Reactivity of the isocyano group towards nucleophiles",
abstract = "AgCNBH2CN and AgCNBH(CN)2 were synthesized with AgCN in Me2S from Me2S·BH2CN and 4-cyanopyridine·BH(CN)2, respectively. These silver complexes were transformed into Na[BH2(CN)NC] and Na[BH(CN)2NC] salts. In these hydrolytically very stable borates the isocyano group proved to be the most reactive site. This observation was demonstrated by reactions with nucleophiles, namely H2S, NH4N3 and NH4SCN. In the first two cases isocyano group underwent transformation into -N(H)-C(H)=S and -1-(5H)tetrazolyl groups, respectively, which remarkably increase the stability of hydroborates towards acidic hydrolysis. Unlike alkyl- or arylisocyanides, isocyano groups here do not form ring in reaction with NH4SCN, but most probably transform into -N=C(H)-NCS groups. All compounds, including the E- and Z-isomers (where appropriate), were characterized by IR, 1H, 11B and 13C NMR spectroscopy.",
keywords = "Cyanohydroisocyanoborates, Cyanohydrotetrazolylborates, Cyanohydrothioformamidoborates, E, Multinuclear NMR, Z-isomerism",
author = "B{\'e}la Gy{\^o}ri and Z. Berente and Istv{\'a}n L{\'a}z{\'a}r",
year = "1998",
month = "8",
day = "31",
language = "English",
volume = "17",
pages = "3175--3180",
journal = "Polyhedron",
issn = "0277-5387",
publisher = "Elsevier Limited",
number = "18",

}

TY - JOUR

T1 - Synthesis and characterization of cyanohydroisocyanoborates. Reactivity of the isocyano group towards nucleophiles

AU - Gyôri, Béla

AU - Berente, Z.

AU - Lázár, István

PY - 1998/8/31

Y1 - 1998/8/31

N2 - AgCNBH2CN and AgCNBH(CN)2 were synthesized with AgCN in Me2S from Me2S·BH2CN and 4-cyanopyridine·BH(CN)2, respectively. These silver complexes were transformed into Na[BH2(CN)NC] and Na[BH(CN)2NC] salts. In these hydrolytically very stable borates the isocyano group proved to be the most reactive site. This observation was demonstrated by reactions with nucleophiles, namely H2S, NH4N3 and NH4SCN. In the first two cases isocyano group underwent transformation into -N(H)-C(H)=S and -1-(5H)tetrazolyl groups, respectively, which remarkably increase the stability of hydroborates towards acidic hydrolysis. Unlike alkyl- or arylisocyanides, isocyano groups here do not form ring in reaction with NH4SCN, but most probably transform into -N=C(H)-NCS groups. All compounds, including the E- and Z-isomers (where appropriate), were characterized by IR, 1H, 11B and 13C NMR spectroscopy.

AB - AgCNBH2CN and AgCNBH(CN)2 were synthesized with AgCN in Me2S from Me2S·BH2CN and 4-cyanopyridine·BH(CN)2, respectively. These silver complexes were transformed into Na[BH2(CN)NC] and Na[BH(CN)2NC] salts. In these hydrolytically very stable borates the isocyano group proved to be the most reactive site. This observation was demonstrated by reactions with nucleophiles, namely H2S, NH4N3 and NH4SCN. In the first two cases isocyano group underwent transformation into -N(H)-C(H)=S and -1-(5H)tetrazolyl groups, respectively, which remarkably increase the stability of hydroborates towards acidic hydrolysis. Unlike alkyl- or arylisocyanides, isocyano groups here do not form ring in reaction with NH4SCN, but most probably transform into -N=C(H)-NCS groups. All compounds, including the E- and Z-isomers (where appropriate), were characterized by IR, 1H, 11B and 13C NMR spectroscopy.

KW - Cyanohydroisocyanoborates

KW - Cyanohydrotetrazolylborates

KW - Cyanohydrothioformamidoborates

KW - E

KW - Multinuclear NMR

KW - Z-isomerism

UR - http://www.scopus.com/inward/record.url?scp=0039400199&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0039400199&partnerID=8YFLogxK

M3 - Article

VL - 17

SP - 3175

EP - 3180

JO - Polyhedron

JF - Polyhedron

SN - 0277-5387

IS - 18

ER -