Helicity Control in the Preparation of Chiral Co-crystals from Tryptamine and Achiral Carboxylic Acids by Pseudo-seeding
- 1 January 2001
- journal article
- research article
- Published by Taylor & Francis in Supramolecular Chemistry
- Vol. 13 (1) , 137-142
- https://doi.org/10.1080/10610270108034889
Abstract
Chiral crystals of tryptamine and achiral carboxylic acids such as p-chlorobenzoic acid, cinnamic acid, p-chlorocinnarnic acid and p-methylcinnamic acid were prepared by crystallization from the solutions of both components. All the crystals belonged to typical chiral space group P212121. The crystal chirality is generated through the formation of a unidirectional twofold helix between the two components through quaternary ammonium salt interaction and hydrogen bonding in the lattice. This kind of spontaneous crystallization necessarily gives crystals of both clockwise and counterclockwise helicites. Here, pseudo-seeding based on utilizing these crystals as seed crystals was examined, resulting in successful helicity control in crystallization from solutions of tryptamine and different carboxylic acids.Keywords
This publication has 16 references indexed in Scilit:
- Chiral Crystallization of Achiral Organic Compounds. Generation of Chirality Without Chiral Environment (Part 1).Journal of Synthetic Organic Chemistry, Japan, 1998
- Chiral Crystallization of Achiral Organic Compounds. Generation of Chirality without Chiral Environment. (Part 2).Journal of Synthetic Organic Chemistry, Japan, 1998
- Synthesis, Structure, and Discrimination of Chiral Bimolecular Crystals by Using Diphenylacetic Acid and Aza Aromatic CompoundsThe Journal of Organic Chemistry, 1997
- Absolute Asymmetric Synthesis from Achiral Molecules in the Chiral Crystalline EnvironmentChemistry – A European Journal, 1997
- Generation of Chirality in a Two-Component Molecular Crystal of Acridine and Diphenylacetic Acid and Its Absolute Asymmetric Photodecarboxylating CondensationJournal of the American Chemical Society, 1996
- An Absolute Asymmetric Synthesis of the [2 + 2] Cycloadduct via Single Crystal-to-Single Crystal Transformation by Charge-Transfer Excitation of Solid-State Molecular Complexes Composed of Arylolefins and Bis[1,2,5]thiadiazolotetracyanoquinodimethaneJournal of the American Chemical Society, 1994
- Design of polymeric inhibitors for the control of crystal polymorphism. Induced enantiomeric resolution at racemic histidine by crystallization at 25.degree.CJournal of the American Chemical Society, 1987
- Growth and Dissolution of Organic Crystals with “Tailor‐Made” Inhibitors—Implications in Stereochemistry and Materials ScienceAngewandte Chemie International Edition in English, 1985
- Asymmetric synthesis via reactions in chiral crystalsAccounts of Chemical Research, 1979
- Reactions in chiral crystals. Optically active heterophotodimer formation from chiral single crystalsJournal of the American Chemical Society, 1973