Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate)
Trimethyl citrate, C9H14O7 (systematic name: trimethyl 2-hydroxypropane-1,2,3-tricarboxylate), 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...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2018-09-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989018011222 |
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| author | Rami Y. Morjan Said M. El-Kurdi Jannat N. Azarah Neda A. Eleiwa Omar S. Abu-Teim Adel M. Awadallah James Raftery John M. Gardiner |
| author_facet | Rami Y. Morjan Said M. El-Kurdi Jannat N. Azarah Neda A. Eleiwa Omar S. Abu-Teim Adel M. Awadallah James Raftery John M. Gardiner |
| author_sort | Rami Y. Morjan |
| collection | DOAJ |
| description | Trimethyl citrate, C9H14O7 (systematic name: trimethyl 2-hydroxypropane-1,2,3-tricarboxylate), 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 carboxylate group and the hydroxy 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 molecules stacked along the c-axis direction. |
| first_indexed | 2024-12-20T15:57:16Z |
| format | Article |
| id | doaj.art-35880002a57d45478dfb347045f5d885 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T15:57:16Z |
| publishDate | 2018-09-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-35880002a57d45478dfb347045f5d8852022-12-21T19:34:24ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902018-09-017491362136510.1107/S2056989018011222sj5563Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate)Rami Y. Morjan0Said M. El-Kurdi1Jannat N. Azarah2Neda A. Eleiwa3Omar S. Abu-Teim4Adel M. Awadallah5James Raftery6John M. Gardiner7Department of Chemistry, Islamic University of Gaza, Gaza PO Box 108, PalestineDepartment of Chemistry, Islamic University of Gaza, Gaza PO Box 108, PalestineDepartment of Chemistry, Islamic University of Gaza, Gaza PO Box 108, PalestineDepartment of Chemistry, Al-Azhar University of Gaza, Gaza PO Box 1277, PalestineDepartment of Chemistry, Al-Azhar University of Gaza, Gaza PO Box 1277, PalestineDepartment of Chemistry, Islamic University of Gaza, Gaza PO Box 108, PalestineSchool of Chemistry, The University of Manchester, Brunswick Street, Manchester M13 9PL, UKManchester Institute of Biotechnology, School of Chemistry and EPS, The University of Manchester, Manchester M1 7DN, UKTrimethyl citrate, C9H14O7 (systematic name: trimethyl 2-hydroxypropane-1,2,3-tricarboxylate), 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 carboxylate group and the hydroxy 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 molecules stacked along the c-axis direction.http://scripts.iucr.org/cgi-bin/paper?S2056989018011222crystal structuretrimethyl citratehydrogen bondsinversion dimersring motifs |
| spellingShingle | Rami Y. Morjan Said M. El-Kurdi Jannat N. Azarah Neda A. Eleiwa Omar S. Abu-Teim Adel M. Awadallah James Raftery John M. Gardiner Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate) Acta Crystallographica Section E: Crystallographic Communications crystal structure trimethyl citrate hydrogen bonds inversion dimers ring motifs |
| title | Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate) |
| title_full | Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate) |
| title_fullStr | Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate) |
| title_full_unstemmed | Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate) |
| title_short | Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate) |
| title_sort | inversion dimers dominate the crystal packing in the structure of trimethyl citrate trimethyl 2 hydroxypropane 1 2 3 tricarboxylate |
| topic | crystal structure trimethyl citrate hydrogen bonds inversion dimers ring motifs |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989018011222 |
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