Tricyanomethane and its Salts with Nitrogen Bases: A Correction of Sixteen Reports

被引:8
作者
Banert, Klaus [1 ]
Hagedorn, Manfred [1 ]
机构
[1] Tech Univ Chemnitz, Organ Chem, Str Nationen 62, D-09111 Chemnitz, Germany
关键词
exclusion of structures; spectroscopic characterization; tricyanomethane; tricyanomethanide salts; unstable compounds; NANOSTRUCTURED MOLTEN-SALT; 1-METHYLIMIDAZOLIUM TRICYANOMETHANIDE; CATALYTIC APPLICATION; CYANOFORM; EXISTENCE; ACID;
D O I
10.1055/s-0037-1611846
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 16 articles, dealing with formation of tricyanomethanide salts from nitrogen bases (amines) and tricyanomethane, turned out to be wrong because no tricyanomethane or similar compounds are used and no tricyanomethanide salts are prepared. This statement is based mainly on the recently published spectroscopic data and depicted spectra, which are completely incompatible with the claimed structures. Some of the tricyanomethanide salts are now synthesized from nitrogen heterocycles and tricyanomethane or other precursors. The corresponding products show plausible spectroscopic data and physical properties, which are entirely different to those previously reported.
引用
收藏
页码:1427 / 1430
页数:4
相关论文
共 43 条
[1]  
[Anonymous], 1896, Ber. Dtsch. Chem. Ges.
[2]   Novel nano molten salt tetra-2,3-pyridiniumporphyrazinato-oxo-vanadium tricyanomethanide as a vanadium surface-free phthalocyanine catalyst: Application to Strecker synthesis of α-aminonitrile derivatives [J].
Baghery, Saeed ;
Zolfigol, Mohammad Ali ;
Safaiee, Maliheh ;
Alonso, Diego A. ;
Khoshnood, Abbas .
APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (11)
[3]   RETRACTED: [TEATNM] and [TEATCM] as novel catalysts for the synthesis of pyridine-3,5-dicarbonitriles via anomeric-based oxidation (Retracted Article) [J].
Baghery, Saeed ;
Zolfigol, Mohammad Ali ;
Maleki, Farahnaz .
NEW JOURNAL OF CHEMISTRY, 2017, 41 (17) :9276-9290
[4]   {[1,4-DHPyrazine][C(CN)3]2} as a New Nano Molten Salt Catalyst for the Synthesis of Novel Piperazine Based bis(4-hydroxy-2H-chromen-2-one) Derivatives [J].
Baghery, Saeed ;
Zolfigol, Mohammad Ali ;
Schirhagl, Romana ;
Hasani, Masoumeh .
CATALYSIS LETTERS, 2017, 147 (08) :2083-2099
[5]   Application of Triphenylammonium Tricyanomethanide as an Efficient and Recyclable Nanostructured Molten-Salt Catalyst for the Synthesis of N-Benzylidene-2-arylimidazo[1,2-a] pyridin-3-amines [J].
Baghery, Saeed ;
Zolfigol, Mohammad Ali ;
Schirhagl, Romana ;
Hasani, Masoumeh .
SYNLETT, 2017, 28 (10) :1173-1176
[6]   AB-INITIO APPROACH TO CYANOFORM PROBLEM [J].
BAK, B ;
BJORKMAN, C .
JOURNAL OF MOLECULAR STRUCTURE, 1975, 25 (01) :131-140
[7]   EXISTENCE OF GASEOUS CYANOFORM AS OBSERVED BY MICROWAVE-SPECTRA [J].
BAK, B ;
SVANHOLT, H .
JOURNAL OF MOLECULAR STRUCTURE, 1977, 37 (01) :153-156
[8]   Tricyanomethane and Its Ketenimine Tautomer: Generation from Different Precursors and Analysis in Solution, Argon Matrix, and as a Single Crystal [J].
Banert, Klaus ;
Chityala, Madhu ;
Hagedorn, Manfred ;
Beckers, Helmut ;
Stueker, Tony ;
Riedel, Sebastian ;
Rueffer, Tobias ;
Lang, Heinrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (32) :9582-9586
[9]   PHOTOELECTRON-SPECTRA AND MOLECULAR-PROPERTIES .110. TRICYANOMETHANE DERIVATIVES X-C(CN)3 [J].
BOCK, H ;
DAMMEL, R .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1987, 42 (03) :315-322
[10]   CYANOCARBON CHEMISTRY .23. IONIZATION BEHAVIOR OF CYANOCARBON ACIDS [J].
BOYD, RH .
JOURNAL OF PHYSICAL CHEMISTRY, 1963, 67 (04) :737-&