Unknown

Dataset Information

0

Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hy-droxy-propane-1,2,3-tri-carboxyl-ate).


ABSTRACT: Trimethyl citrate, C9H14O7 (systematic name: trimethyl 2-hy-droxy-propane-1,2,3-tri-carboxyl-ate), 2, was prepared by the esterification of citric acid and methanol in the presence of thionyl chloride at 273 K. The bond lengths and angles in 2 compare closely with those observed in citric acid. The C-C bonds adjacent to the terminal carboxyl groups are significantly shorter than those around the central C atom. The central carboxyl-ate group and the hy-droxy group occur in the normal planar arrangement with an r.m.s. deviation of 0.0171 Å from the mean plane involving all six atoms in the central unit. The crystal structure is almost completely dominated by the formation of inversion dimers through an O-H⋯O hydrogen bond, together with an extensive array of weaker C-H⋯O contacts. These generate a three-dimensional network structure with mol-ecules stacked along the c-axis direction.

SUBMITTER: Morjan RY 

PROVIDER: S-EPMC6127686 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

altmetric image

Publications

Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hy-droxy-propane-1,2,3-tri-carboxyl-ate).

Morjan Rami Y RY   El-Kurdi Said M SM   Azarah Jannat N JN   Eleiwa Neda A NA   Abu-Teim Omar S OS   Awadallah Adel M AM   Raftery James J   Gardiner John M JM  

Acta crystallographica. Section E, Crystallographic communications 20180824 Pt 9


Trimethyl citrate, C<sub>9</sub>H<sub>14</sub>O<sub>7</sub> (systematic name: trimethyl 2-hy-droxy-propane-1,2,3-tri-carboxyl-ate), <b>2</b>, was prepared by the esterification of citric acid and methanol in the presence of thionyl chloride at 273 K. The bond lengths and angles in <b>2</b> compare closely with those observed in citric acid. The C-C bonds adjacent to the terminal carboxyl groups are significantly shorter than those around the central C atom. The central carboxyl-ate group and the  ...[more]

Similar Datasets

| S-EPMC4647391 | biostudies-literature
| S-EPMC2968398 | biostudies-literature
| S-EPMC3009217 | biostudies-literature
| S-EPMC2970973 | biostudies-literature
| S-EPMC3212311 | biostudies-literature
| S-EPMC2968371 | biostudies-literature
| S-EPMC2961753 | biostudies-literature
| S-EPMC6044983 | biostudies-literature
| S-EPMC2983924 | biostudies-literature
| S-EPMC2979147 | biostudies-literature