Tetramethylammonium (Z)-N′-cyanocarbamimidate

Abstract

In the structure of the tetramethyl ammonium salt of cyanourea, C4H12N+·C2H2N3O−, the N—C and O—C bond distances in the cyano and keto groups are in the normal range for such a moieties at 1.1641 (18) and 1.2550 (16) Å. However, the bonds about the central C and N atoms are much shorter than would be expected for single bonds and indicate that there is considerable electron delocalization in the anion as was also found in the silver salt. The NH2group is coplanar with the central N2CO core, in contrast with the nitrile group where the dihedral angle between the N—C—N and N2CO planes is 36.5 (3)°. The packing of the cations and anions in the unit cell involves N—H...O hydrogen bonds between anions characterized by anR22(8) motif, as well as N—H...O hydrogen bonds between anions and C—H...O interactions between both cations and anions, forming anR33(14) pattern.

Document Details

Document Type
Pub Defense Publication
Publication Date
Nov 04, 2021
Source ID
10.1107/s2414314621010981

Entities

People

  • Andrew P Purdy
  • Ray J Butcher

Organizations

  • Office of Naval Research

Tags

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry
  • Quantum Chemistry

Technology Areas

  • Microelectronics