The crystal structure of methacholine chloride, C8H18ClNO2

Muller, Kina; Hosten, Eric C.; Betz, Richard

doi:10.1515/ncrs-2020-0526

Cited by 1 publication

(1 citation statement)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A survey of the Cambridge Structural Database (version 5.45, November, 2023;Groom et al, 2016). yields only two known prior examples of structures containing 2CLEA + : an (Mo 2 O 2 Cl 8 ) 2À salt (CSD refcode POSWAX; Marchetti et al, 2015), in which the gauche conformation is found, and a chloride salt (CSD refcode: URORUR; Muller et al, 2021) where the anti conformation is found, albeit with a disordered alkyl chain. For 3CLPA + , besides the aforementioned chloride salt there is one other structure containing 3-chloro-N,N-propan-1-amine as a ligand in a di(�-hydrido) dialuminium complex (CSD refcode: NIGGOZ; Andrews et al, 1997) where the gauche conformation is also found.…”

Section: Database Surveymentioning

confidence: 99%

Bis(2-chloro-N,N-dimethylethan-1-aminium) tetrachloridocobaltate(II) and tetrachloridozincate(II)

McGinness,

Minton,

White

et al. 2024

Acta Cryst E

View full text Add to dashboard Cite

The few examples of structures containing the 2-chloro-N,N-dimethylethan-1-aminium or 3-chloro-N,N-dimethylpropan-1-aminium cations show a competition between gauche and anti conformations for the chloroalkyl chain. To explore further the conformational landscape of these cations, and their possible use as molecular switches, the title salts, (C4H11ClN)2[CoCl4] and (C4H11ClN)2[ZnCl4], were prepared and structurally characterized. Details of both structures are in close agreement. The inorganic complex exhibits a slightly flattened tetrahedral geometry that likely arises from bifurcated N—H hydrogen bonds from the organic cations. The alkyl chain of the cation is disordered between gauche and anti conformations with the gauche conformation occupancy refined to 0.707 (2) for the cobaltate. The gauche conformation places the terminal Cl atom at a tetrahedral face of the inorganic complex with a contact distance of 3.7576 (9) Å to the Co2+ center. The anti conformation places the terminal Cl atom at a contact distance to a neighboring anti conformation terminal Cl atom that is ∼1 Å less than the sum of the van der Waals radii. Thus, if the anti conformation is present at a site, then the nearest neighbor must be gauche. DFT geometry optimizations indicate the gauche conformation is more stable in vacuo by 0.226 eV, which reduces to 0.0584 eV when calculated in a uniform dielectric. DFT geometry optimizations for the unprotonated molecule indicate the anti conformation is stabilized by 0.0428 eV in vacuo, with no strongly preferred conformation in uniform dielectric, to provide support to the notion that this cation could function as a molecular switch via deprotonation.

show abstract

Section: Database Surveymentioning

confidence: 99%