Home
Resources
Publications
Weak Hydrogen Bonding and Fluorous Interactions in the Chloride and Bromide Salts of 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium

Weak Hydrogen Bonding and Fluorous Interactions in the Chloride and Bromide Salts of 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium

Norman Lu, Rong Jyun Wei, Kwan Yu Lin, Mani Alagesan, Yuh Sheng Wen, Ling Kang Liu

Acta Crystallogr C Struct Chem. 2017 Apr 1;73(Pt 4):343-349.

PMID: 28378719

Abstract:

Neutralization of 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridine with hydrohalo acids HX (X = Cl and Br) yielded the pyridinium salts 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium chloride, C9H10F4NO+·Cl-, (1), and 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium bromide, C9H10F4NO+·Br-, (2), both carrying a fluorous side chain at the para position of the pyridinium ring. Single-crystal X-ray diffraction techniques revealed that (1) and (2) are isomorphous. The halide anions accept four hydrogen bonds from N-H, ortho-C-H and CF2-H groups. Two cations and two anions form a centrosymmetric dimeric building block, utilizing complimentary N-H...X...H-Csp3 connections. These dimers are further crosslinked, utilizing another complimentary Csp2-H...X...H-Csp2 connection. The pyridinium rings are π-stacked, forming columns running parallel to the a axis that make angles of ca 44-45° with the normal to the pyridinium plane. There are also supramolecular C-H...F-C interactions, namely bifurcated C-H...F and bifurcated C-F...H interactions; additionally, one type II C-F...F-C halogen bond has been observed.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS777111	(12-Dodecylphosphonic acid)pyridinium bromide			Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: