Metabolic pathways of dithiocarbamates from laboratory powder diffraction data

V V Chernyshev; K A Paseshnichenko; V A Makarov; E J Sonneveld; H Schenk

doi:10.1107/s0108270100013457

Metabolic pathways of dithiocarbamates from laboratory powder diffraction data

Acta Crystallogr C. 2001 Jan;57(Pt 1):72-5. doi: 10.1107/s0108270100013457.

Authors

V V Chernyshev¹, K A Paseshnichenko, V A Makarov, E J Sonneveld, H Schenk

Affiliation

¹ Chemistry Department, Moscow State University, 119899 Moscow, Russia. cher@biocryst.phys.msu.su

PMID: 11173404
DOI: 10.1107/s0108270100013457

Abstract

In order to correlate the reactivity and molecular structures of dithiocarbamates, the crystal structures of 6-dimethylamino-5-nitropyrimidin-4-yl N,N-diethyldithiocarbamate, C11H17N5O2S2, (Ia), and 6-methylamino-5-nitropyrimidin-4-yl N,N-diethyldithiocarbamate, C10H15N5O2S2, (Ib), and of the product of thermolysis of (Ib), namely 4-diethylamino-6-methylamino-5-nitropyrimidinium chloride monohydrate, C9H16N5(O2)(+).Cl(-).H2O, (II), have been determined from X-ray laboratory powder diffraction data. Conformational preferences in (Ia) and (Ib) were studied on the density functional theory (DFT) level. Deviation of the reaction centre of the molecule from planarity and breakage of the secondary S...O contact cause switching between two alternative pathways of thermolysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Infective Agents / chemistry*
Anti-Infective Agents / metabolism
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Thiocarbamates / chemistry*
Thiocarbamates / metabolism*
X-Ray Diffraction

Substances

Anti-Infective Agents
Thiocarbamates