Related Experiment Video
Updated: Aug 4, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
N-Ethyl-2-[1-(2-hy-droxy-4-methyl-phen-yl)ethyl-idene]hydrazinecarbo-thio-amide
Brian J Anderson1, Jeffrey R Hall1, Jerry P Jasinski1
1Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA.
Abstract:
The title compound, C12H17N3OS, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the benzene ring and the hydrazinecarbo-thio-amide group are 6.9 (4) and 37.2 (5)° in mol-ecules A and B, respectively. An intra-molecular O-H⋯N hydrogen bond is observed in each mol-ecule. This serves to maintain an approximately planar conformation for mol-ecule A, but leaves a significant twist between these two groups in mol-ecule B. In the crystal, a weak N-H⋯S inter-action is observed, forming inversion dimers among the B mol-ecules and resulting in an R 2 (2)(8) motif. These dimers are further inter-connected by weak N-H⋯O and C-H⋯O inter-molecular inter-actions, forming chains along [011].
More Related Videos
Related Concept Videos
Preparation and Reactions of Sulfides
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Structures 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 unhybridized p...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Diazonium Group Substitution: –OH and –H
Nomenclature 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.

