Pseudoacids. II. 2-acylbenzoic acid derivatives

被引:7
作者
Valente, EJ [1 ]
Martin, SB [1 ]
Sullivan, LD [1 ]
机构
[1] Mississippi Coll, Dept Chem, Clinton, MS 39058 USA
关键词
D O I
10.1107/S0108768197012020
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Structures of derivatives of cyclic o-acylbenzoic acids, including the chloride, endo- and exocyclic amides, eaters and anhydrides, are examined. 3-Chloro-1(3H)-isobenzofuranone (1), orthorhombic, Pbca, a = 11.616 (5), b = 8.120 (3), c = 15.640 (9) Angstrom; 3-methoxy-3-phenyl-1(3H)-isobenzofuranone (3), orthorhombic, P2(1)2(1)2(1), a = 6.923 (2), b = 8.291 (4), c = 21.551 (8) Angstrom; 3-hydroxy-3-phenyl-N-propyl-1(3H)-isoindolone (4), orthorhombic, P2(1)2(1)2(1), a = 8.662 (4), b = 9.551 (7), c = 17.649 (14) Angstrom; 3-(N-morpholino)-1(3H)-isobenzofuranone (5), triclinic, P (1) over bar, a = 6.172 (4), b = 11.163 (7), c = 17.33 (2) Angstrom, alpha = 105.91 (6), beta = 99.85 (6), gamma = 97.57 (5)degrees; 3-(2'-benzoylbenzoyloxy)-3-phenyl-1(3H)-isobenzofuranone (7), triclinic, P (1) over bar, a = 9.694 (3), b = 10.505 (4), c = 11.163 (4) Angstrom, alpha = 80.58 (3), beta = 80.41 (3), gamma = 76.49 (3)degrees; bis[1(3H)-isobenzofuranone-3-yl]ether (8), monoclinic, 12/a, a = 15.31(2), b = 6.111(12), c = 28.30 (5) Angstrom, beta = 101.61 (12)degrees. An open oxoacid tertiary amide is also described: N-morpholino 2'-benzoylbenzamide (6): monoclinic, P2(1)/c, a = 6.844(4), b = 15.696(8), c = 14.154 (7) Angstrom, beta = 99.43(4)degrees. Pseudoacid derivatives form planar isobenzofuran and isoindole rings, and the former aldehyde/ketone carbon-heteroatom endocyclic and exocyclic bond distances show bond length variations which correlate with the relative basicities of the attached groups. Structures of both endocyclic and exocyclic nitrogen pseudoamides are reported as well as examples of the normal-pseudoanhydride and the dipseudoanhydride.
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页码:264 / 276
页数:13
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