Notes: Preparation of 2-Imino- and 2-Nitrimine-1,3-diazacycloalkanes

Hafner, L. S.; Evans, Robert

doi:10.1021/jo01090a626

Cited by 12 publications

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“…X-ray diffraction study on a single crystal of α-2-methyl-1-nitroisothiourea (α-C 2 H 5 SN 3 O 2 ) unexpectedly revealed that the molecule α-2-methyl-1-nitroisothiourea is unlike other nitrimines. ,,,, It adopts conformation C, the structure of the nitroguanyl fragment in α-2-methyl-1-nitroisothiourea, because the sulfur atom unlike that in other nitrimines can be involved in nitrimine conjugation. The α-2-methyl-1-nitroisothiourea belongs to the triclinic system space group P 1̅, with unit cell parameters a = 7.355(1) Α̊, b = 7.468(1) Α̊, c = 5.1659(5) Α̊, α = 105.40(1)°, β = 94.43(1)°, γ = 86.50(1)°, and Z = 2 (see ref ).…”

Section: Theoretical Calculationmentioning

confidence: 99%

“…Several patents contain an extensive list of substituents, biological activities and organisms, both in the animal kingdom and in the plant kingdom. A known method for preparation of nitroguanidine derivatives is based on the reaction of 2-methyl-1-nitroisothiourea with amines. − A great number of nitroguanidines having various aliphatic and aromatic substituents have been synthesized. − This extensive list of applications leads to the synthesis of a vast number of new compounds, often available in the market at low prices. The synthetic nitroguanidine derivative can be used as alternative to the traditional adenine-containing cytokinins used in plant tissue culture.…”

Section: Introductionmentioning

confidence: 99%

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Ab Initio Calculation of the Electronic Band Structure, Density of States and Optical Properties of α-2-Methyl-1-nitroisothiourea

et al. 2009

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The electronic and optical properties of alpha-2-methyl-1-nitroisothiourea have been studied using a full potential linear augmented plane wave method within density-functional theory along with the Engel-Vosko exchange correlation function. The structural data obtained by Vasil'ev et al. [Vasil'ev, A. D.; Astakhov, A. M.; Gelemurzina, I. V.; Stepanov, R. S. Dokl. Chem. 2001, 379, (4-6), 232-235; translated from Dokl. Akad. Nauk 2001, 379 (6), 781-784] from X-ray diffraction was used. Our calculations show that the valence band maximum (VBM) is located at the T and the conduction band minimum (CBM) is located at the R point of the Brillouin zone, resulting in an indirect energy gap of 3.1 eV. The calculated partial density of states shows that the upper valence band and the lower conduction band arise predominantly from the O-p, N-p and S-p states. The compound has a large uniaxial dielectric anisotropy and a large negative birefringence.

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Section: Theoretical Calculationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ab Initio Calculation of the Electronic Band Structure, Density of States and Optical Properties of α-2-Methyl-1-nitroisothiourea

et al. 2009

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“…Several procedures for the synthesis of 2-nitroiminoimidazolidine were developed. Hafner and Evans [116] obtained this compound in 72.1% yield by reaction of S-methyl-N-nitroisothiourea (95) Presumably, the most convenient procedure for the synthesis of 2-nitroiminoimidazolidine (97) is that proposed by McKay and Wright [118,119]. According to the authors, compound 97 is formed by reaction of nitroguanidine (99) with ethylenediamine dihydrochloride (100) and potassium hydroxide in water on heating (Scheme 37).…”

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confidence: 99%