Crystal Structures of Sulfobetaine-8 Solvates: Bend Hydrophobic Chains and Doubly Charge-Assisted Hydrogen Bonds N<sup>+</sup>CH⋯<sup>−</sup>O<sub>3</sub>S
Three novel solvatomorphs (C<sub>13</sub>H<sub>29</sub>NO<sub>3</sub>S•CH<sub>3</sub>OH, <b>1</b>; C<sub>13</sub>H<sub>29</sub>NO<sub>3</sub>S•0.113(H<sub>2</sub>O), <b>2</b>; C<...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-12-01
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| Series: | Crystals |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4352/14/12/1062 |
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| Summary: | Three novel solvatomorphs (C<sub>13</sub>H<sub>29</sub>NO<sub>3</sub>S•CH<sub>3</sub>OH, <b>1</b>; C<sub>13</sub>H<sub>29</sub>NO<sub>3</sub>S•0.113(H<sub>2</sub>O), <b>2</b>; C<sub>13</sub>H<sub>29</sub>NO<sub>3</sub>S•0.038(H<sub>2</sub>O), <b>3</b>) of zwitterionic sulfobetaine-8 were obtained and their structures were determined using single-crystal X-Ray diffraction. In all cases dimethyl–amino substituted hydrophobic chains -(CH<sub>2</sub>)<sub>3</sub>-N<sup>+</sup>Me<sub>2</sub>-(CH<sub>2</sub>)<sub>7</sub>-Me exhibit kinks at nitrogen atoms resulted from strong intra- and intermolecular CH⋯O hydrogen bonds between negatively charged sulfonic anion <sup>-</sup>O<sub>3</sub>S- and positively charged tetraalkylammonium fragments. Periodic (solid state) DFT calculations for structure 1 showed that the energy of the intermolecular hydrogen bonds CH…O is very high, at about 17 kJ/mol. In hydrates <b>2</b> and <b>3</b>, water molecules play the structure-forming role since they interconnect hydrophobic layers by HOH<sup>…-</sup>O<sub>3</sub>S hydrogen bonds. The location of only partially occupied water molecules in the interlayer space leads to low stability of both crystals <b>2</b> and <b>3</b> in open air. |
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| ISSN: | 2073-4352 |