Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy
X-Ray crystallography demonstrates that the guest molecule binding cavity within the molecular receptor ligand 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane, (S)-thpec12, is a poorly defined conical region stabilized by three O-H center dot center dot center dot O hyd...
| Main Authors: | , , , , |
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| Format: | Journal Article |
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CSIRO Publishing
2006
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| Online Access: | http://hdl.handle.net/20.500.11937/27491 |
| _version_ | 1848752278484287488 |
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| author | Smith, C. Buntine, Mark Lincoln, S. Taylor, M. Wainwright, K. |
| author_facet | Smith, C. Buntine, Mark Lincoln, S. Taylor, M. Wainwright, K. |
| author_sort | Smith, C. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | X-Ray crystallography demonstrates that the guest molecule binding cavity within the molecular receptor ligand 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane, (S)-thpec12, is a poorly defined conical region stabilized by three O-H center dot center dot center dot O hydrogen bonds and a single O-H center dot center dot center dot N hydrogen bond. Two similar, but crystallographically independent, molecules exist within the unit cell. Ab initio calculations, using Gaussian 03 (LanL2DZ basis set at the Hartree-Fock level of theory), predict that these have steric energies of 97.73 and 97.06 kJ mol(-1), respectively, above that of the minimum energy ( gas phase) conformer of the same hydrogen-bonding configuration, which is believed to be the structure of global minimum energy. The mean of these energies (97.4 kJ mol(-1)) represents a best estimate of the crystal packing energy for (S)-thpec12, some of which is seen to be expended in rotating the phenyl rings away from the positions favoured in the gas phase. The ability of the Cd-II complex of (S)-thpec12 to act as a molecular receptor for aromatic anions is demonstrated by the isolation of two inclusion compounds in which p-nitrophenolate and anthraquinone-2-sulfonate are retained. |
| first_indexed | 2025-11-14T08:06:05Z |
| format | Journal Article |
| id | curtin-20.500.11937-27491 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:06:05Z |
| publishDate | 2006 |
| publisher | CSIRO Publishing |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-274912017-09-13T15:06:35Z Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy Smith, C. Buntine, Mark Lincoln, S. Taylor, M. Wainwright, K. Inclusion chemistry X-Ray crystallography demonstrates that the guest molecule binding cavity within the molecular receptor ligand 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane, (S)-thpec12, is a poorly defined conical region stabilized by three O-H center dot center dot center dot O hydrogen bonds and a single O-H center dot center dot center dot N hydrogen bond. Two similar, but crystallographically independent, molecules exist within the unit cell. Ab initio calculations, using Gaussian 03 (LanL2DZ basis set at the Hartree-Fock level of theory), predict that these have steric energies of 97.73 and 97.06 kJ mol(-1), respectively, above that of the minimum energy ( gas phase) conformer of the same hydrogen-bonding configuration, which is believed to be the structure of global minimum energy. The mean of these energies (97.4 kJ mol(-1)) represents a best estimate of the crystal packing energy for (S)-thpec12, some of which is seen to be expended in rotating the phenyl rings away from the positions favoured in the gas phase. The ability of the Cd-II complex of (S)-thpec12 to act as a molecular receptor for aromatic anions is demonstrated by the isolation of two inclusion compounds in which p-nitrophenolate and anthraquinone-2-sulfonate are retained. 2006 Journal Article http://hdl.handle.net/20.500.11937/27491 10.1071/CH05275 CSIRO Publishing restricted |
| spellingShingle | Inclusion chemistry Smith, C. Buntine, Mark Lincoln, S. Taylor, M. Wainwright, K. Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy |
| title | Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy |
| title_full | Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy |
| title_fullStr | Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy |
| title_full_unstemmed | Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy |
| title_short | Structure of the molecular receptor 1,4,7,10-tetrakis[(S)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: A combined X-ray crystallographic and theoretical study producing an assessment of the crystal packing energy |
| title_sort | structure of the molecular receptor 1,4,7,10-tetrakis[(s)-2-hydroxy-2-phenylethyl]-1,4,7,10-tetraazacyclododecane: a combined x-ray crystallographic and theoretical study producing an assessment of the crystal packing energy |
| topic | Inclusion chemistry |
| url | http://hdl.handle.net/20.500.11937/27491 |