Conformations and structure studies of sugar lactones in the solid state. Part I. The molecular structure of L-rhamnono- and L-mannono-1,4-lactones.
The crystal structures of L-rhamnono-1,4-lactone (1) and L-mannono-1,4-lactone (2) have been determined by single-crystal X-ray diffraction. Pertinent crystal data are as follows: for 1, orthorhombic, space group P2(1)2(1)2(1), a = 4.8829(2), b = 10.9088(8), c = 13.9758(9) A, V = 734.7(1) A3, Dc = 1.610 g cm-3, Z = 4, R = 0.028 and Rw = 0.035 for 1586 reflections. The lactone ring of 1 adopts an envelope conformation, E3, slightly distorted toward 2T3, with psi = 103.1(7) degrees and q = 0.38(3) A, whereas the lactone ring of 2 adopts a perfect envelope E3 conformation, with psi = 106.6(4) degrees and q = 0.42(4) A. Molecules of 1 and 2 are linked in their crystals through a three dimensional network of O-H ... H hydrogen-bonding interactions that involves all hydroxyl groups as well as the carbonyl oxygen atom.
Shalaby
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Department of Biochemistry, Louisiana State University, Baton Rouge 70803.
Fronczek
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Younathan
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D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray / Q000379:methods; D006860:Hydrogen Bonding; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular
D007783:Lactones; C091284:mannono-1,4-lactone; C091283:rhamnono-1,4-lactone; D015107:4-Butyrolactone