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Halogen Bonding in N-Alkyl-3-halogenopyridinium Salts (CROSBI ID 299485)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Fotović, Luka ; Stilinović, Vladimir Halogen Bonding in N-Alkyl-3-halogenopyridinium Salts // Crystals, 11 (2021), 10; 1240-1256. doi: 10.3390/cryst11101240

Podaci o odgovornosti

Fotović, Luka ; Stilinović, Vladimir

engleski

Halogen Bonding in N-Alkyl-3-halogenopyridinium Salts

We performed a structural study of N-alkylated halogenopyridinium cations to examine whether choice of the N-substituent has any considerable effect on the halogen bonding capability of the cations. For that purpose, we prepared a series of N-ethyl-3-halopyridinium iodides and compared them with their N-methyl-3-halopyridinium analogues. Structural analysis revealed that N-ethylated halogenopyridinium cations form slightly shorter C−X⋯I− halogen bonds with iodide anion. We have also attempted synthesis of ditopic symmetric bis- (3-iodopyridinium) dications. Although successful in only one case, the syntheses have afforded two novel ditopic asymmetric monocations with an iodine atom bonded to the pyridine ring and another on the aliphatic N-substituent. Here, the C−I⋯I− halogen bond lengths involving pyridine iodine atom were notably shorter than those involving an aliphatic iodine atom as a halogen bond donor. This trend in halogen bond lengths is in line with the charge distribution on the Hirshfeld surfaces of the cations—the positive charge is predominantly located in the pyridine ring making the pyridine iodine atom σ-hole more positive than the one on the alkyl chan.

pyridinium cations ; halogen bond ; halogenide anions

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Podaci o izdanju

11 (10)

2021.

1240-1256

objavljeno

2073-4352

10.3390/cryst11101240

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Kemija

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