(5-Meth-oxy-1H-indol-3-yl)acetonitrile
Yu-Hua Ge1, Jin-Feng Li, Yang-Hui Luo
1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|January 20, 2012
Summary
The crystal structure of C(11)H(10)N(2)O reveals a nearly planar ring system. Molecules form zigzag chains through N-H⋯O hydrogen bonds in the crystal lattice.
Area of Science:
- Crystallography
- Molecular structure analysis
- Supramolecular chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic compounds is crucial for predicting their physical and chemical properties.
- Hydrogen bonding plays a significant role in the self-assembly of molecules and the formation of extended structures in the solid state.
Purpose of the Study:
- To determine and analyze the crystal structure of the title compound, C(11)H(10)N(2)O.
- To investigate the planarity of the ring system and the intermolecular interactions present in the crystal.
Main Methods:
- Single-crystal X-ray diffraction was employed to obtain the three-dimensional structural data.
- Analysis of atomic deviations from the mean plane and identification of hydrogen bonding networks.
Main Results:
- The title compound, C(11)H(10)N(2)O, exhibits an approximately planar ring system with minimal deviations for the oxygen and methylene carbon atoms.
- Root-mean-square deviation for the ring system was calculated to be 0.013 Å.
- Intermolecular N-H⋯O hydrogen bonds were observed, linking molecules into zigzag chains along the crystallographic b axis.
Conclusions:
- The crystal structure confirms the near planarity of the C(11)H(10)N(2)O ring system.
- The identified hydrogen bonding pattern dictates the formation of one-dimensional zigzag chains, influencing the compound's solid-state architecture.
Related Concept Videos
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
Naming Amides
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.
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.
01:16Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
01:28Structures of Carboxylic Acid Derivatives
Structure 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...
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...
01:09IUPAC Nomenclature of Ketones
Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
02:39Nomenclature of Alkynes
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
01:19Amines to Amides: Acylation of Amines
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...