Synthesis and crystal structure of 2,2,2-tri-chloroethyl
J Voss1, H G Stammler1, N Sewald1
1Bielefeld University, Department of Chemistry, Universitaetsstr. 25, Bielefeld, 33615, Germany.
Abstract:
An orthogonally addressable 3,6-disubstituted 1,2,4,5-tetra-zine, namely 2,2,2-tri-chloro-ethyl N-{4-[6-(1-hy-droxy-eth-yl)-1,2,4,5-tetra-zin-3-yl]benz-yl}carbamate (C14H14Cl3N5O3), was synthesized and characterized by single-crystal X-ray diffraction. The tetra-zine comprises a free hydroxyl and a 2,2,2-tri-chloro-eth-oxy-carbonyl protected amino group, which gives rise to hydrogen-bonding inter-actions each making the tetra-zine highly linked in the solid state. The carbamate moieties form inter-molecular hydrogen bonds, stacking the tetra-zine mol-ecules above each other, while lateral hydrogen bonds are formed between a tetra-zine N atom and a hydroxyl group, the latter inter-action being a scarcely explored structural feature of 1,2,4,5-tetra-zines.
Related Concept Videos
01:28Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
01:07Radicals: Electronic Structure and Geometry
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
01:34NMR Spectroscopy of Benzene Derivatives