3-Chloro-N,N-dimethylpropan-1-aminium chloride
The organic cation in the title molecular salt, C5H13NCl+·Cl−, exhibits the gauche effect with a C—H bond of the C atom β to the chloro group donating electrons to the antibonding orbital of the C—Cl bond to stabilize the gauche conformation [Cl—C—C—C = −68.6 (6)°], as confirmed by DFT geometry opti...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-01-01
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| Series: | IUCrData |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2414314623000159 |
| _version_ | 1811168165522046976 |
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| author | Marcus R. Bond Sajan Silwal |
| author_facet | Marcus R. Bond Sajan Silwal |
| author_sort | Marcus R. Bond |
| collection | DOAJ |
| description | The organic cation in the title molecular salt, C5H13NCl+·Cl−, exhibits the gauche effect with a C—H bond of the C atom β to the chloro group donating electrons to the antibonding orbital of the C—Cl bond to stabilize the gauche conformation [Cl—C—C—C = −68.6 (6)°], as confirmed by DFT geometry optimizations that show a lengthening of the C—Cl bond relative to that of the anti conformation. Of further interest is the higher point group symmetry of the crystal (\overline{4}), compared that of the that of the molecular cation, which arises from a supramolecular head-to-tail square arrangement of four molecular cations that circulate in a counterclockwise direction when viewed down the tetragonal c axis. |
| first_indexed | 2024-04-10T16:21:30Z |
| format | Article |
| id | doaj.art-942331471fcd4e2d8d4003198a82f214 |
| institution | Directory Open Access Journal |
| issn | 2414-3146 |
| language | English |
| last_indexed | 2024-04-10T16:21:30Z |
| publishDate | 2023-01-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | IUCrData |
| spelling | doaj.art-942331471fcd4e2d8d4003198a82f2142023-02-09T13:29:18ZengInternational Union of CrystallographyIUCrData2414-31462023-01-0181x23001510.1107/S2414314623000159hb44223-Chloro-N,N-dimethylpropan-1-aminium chlorideMarcus R. Bond0Sajan Silwal1Department of Chemistry and Physics, Southeast Missouri State University, Cape Girardeau, MO 63701, USADepartment of Chemistry and Physics, Southeast Missouri State University, Cape Girardeau, MO 63701, USAThe organic cation in the title molecular salt, C5H13NCl+·Cl−, exhibits the gauche effect with a C—H bond of the C atom β to the chloro group donating electrons to the antibonding orbital of the C—Cl bond to stabilize the gauche conformation [Cl—C—C—C = −68.6 (6)°], as confirmed by DFT geometry optimizations that show a lengthening of the C—Cl bond relative to that of the anti conformation. Of further interest is the higher point group symmetry of the crystal (\overline{4}), compared that of the that of the molecular cation, which arises from a supramolecular head-to-tail square arrangement of four molecular cations that circulate in a counterclockwise direction when viewed down the tetragonal c axis.http://scripts.iucr.org/cgi-bin/paper?S2414314623000159crystal structuregauche effectmerohedral twinsupramolecularhyperconjugation |
| spellingShingle | Marcus R. Bond Sajan Silwal 3-Chloro-N,N-dimethylpropan-1-aminium chloride IUCrData crystal structure gauche effect merohedral twin supramolecular hyperconjugation |
| title | 3-Chloro-N,N-dimethylpropan-1-aminium chloride |
| title_full | 3-Chloro-N,N-dimethylpropan-1-aminium chloride |
| title_fullStr | 3-Chloro-N,N-dimethylpropan-1-aminium chloride |
| title_full_unstemmed | 3-Chloro-N,N-dimethylpropan-1-aminium chloride |
| title_short | 3-Chloro-N,N-dimethylpropan-1-aminium chloride |
| title_sort | 3 chloro n n dimethylpropan 1 aminium chloride |
| topic | crystal structure gauche effect merohedral twin supramolecular hyperconjugation |
| url | http://scripts.iucr.org/cgi-bin/paper?S2414314623000159 |
| work_keys_str_mv | AT marcusrbond 3chloronndimethylpropan1aminiumchloride AT sajansilwal 3chloronndimethylpropan1aminiumchloride |