Domagala, Malgorzata and Dubis, Alina T. and Wojtulewski, Slawomir and Zabel, Manfred and Pfitzner, Arno (2022) Hydrogen Bonding in Crystals of Pyrrol-2-yl Chloromethyl Ketone Derivatives and Methyl Pyrrole-2-Carboxylate. CRYSTALS, 12 (11): 1523. ISSN 2073-4352
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The crystal and molecular structure of three derivatives of carbonyl 2-substituted pyrroles was determined by the single crystal X-ray diffraction. There are 2,2-dichloro-1-(1-methyl-1H-pyrrol-2-yl)ethan-1-one (I), 2-chloro-1-(1H-pyrrol-2-yl)ethan-1-one (II) and methyl 1H-pyrrole-2-carboxylate (III). All compounds crystallize with one molecule in the asymmetric unit in P2(1)2(1)2(1) for I and II, and P2(1)/c group for III. Despite the similar structures of the investigated compounds, the hydrogen bonds formed in their crystal structures adopt different H-bond motifs. In structure I, the dimers R-1(2)(5) and R-2(1)(7) form a chain along the b-axis, while in structures II and III, chain C(5) structural motifs are formed. The single point calculations at a omega B97XD/6-311++G(d,p) level of theory indicate that systems with N-HMIDLINE HORIZONTAL ELLIPSISO bonds have greater interaction energies (are more stable) compared with systems featuring C-HMIDLINE HORIZONTAL ELLIPSISO/Cl bonds. A descriptive Hirshfeld analysis showed that the greatest differences are visible for the HMIDLINE HORIZONTAL ELLIPSISH interactions. These HMIDLINE HORIZONTAL ELLIPSISH interactions predominate in structure III, accounting for 45% of the intermolecular interactions, while in structures I and II, they account for only 25%. Although compounds I-II contain Cl-atoms, the percentage of ClMIDLINE HORIZONTAL ELLIPSISCl interactions is rather low. In structure with two Cl-atoms (I), the contribution of the ClMIDLINE HORIZONTAL ELLIPSISCl contacts is 8.7% and for II, the contribution accounts for only 0.4% of the interactions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-SUBSTITUTED PYRROLECARBALDEHYDES; MOLECULAR-ORBITAL METHODS; AB-INITIO; TETRAMETHYLAMMONIUM ION; HALOGEN BOND; BASIS-SETS; AROMATICITY; ABSORPTION; PATTERNS; PERAMINE; crystal structure; hydrogen bond; Hirshfeld surface; pyrrol-2-yl ketone; DFT |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Chair Prof. Dr. Arno Pfitzner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 16 Feb 2024 05:19 |
| Last Modified: | 16 Feb 2024 05:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/57820 |
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