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Structure of 4-carboxy-2-nitrobenzeneboronic acid
S Soundararajan1, E N Duesler, J H Hageman
1Enzon, Inc., S. Plainfield, NJ 07080.
Abstract:
4-(Dihydroxyboryl)-3-nitrobenzoic acid, C7H6BNO6, M(r) = 210.94, monoclinic, P2(1)/n, a = 10.542 (2), b = 6.411 (1), c = 13.105 (4) A, beta = 106.47 (2) degrees, V = 849.3 (4) A3, Z = 4, Dm = 1.65 (flotation in CCl4/1,2-dibromoethane), Dx = 1.649 Mg m-3, lambda(Mo K alpha) = 0.71073 A, mu = 0.135 mm-1, F(000) = 432, T = 293 K, R = 0.0530 for 1328 observed reflections with F > 2 sigma(F). The molecule is flat [the carboxy and nitro groups are rotated 5.8 (4) and 1.9 (4) degrees, respectively, out of the plane] with the boronic acid group almost normal to the plane of the benzene ring, 92.4 (3) degrees. The B atom and one O atom of the nitro group are separated by only 2.457 (4) A implying an interaction that is consistent with observed chemical behavior.
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IUPAC Nomenclature of Carboxylic Acids
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
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...
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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.