Halogen Bonding of (Iodoethynyl)benzene Derivatives in Solution | Zendy

Oliver Dumele∞ | Zendy; Dino Wu | Zendy; Nils Trapp | Zendy; Nancy S. Goroff | Zendy; François Diederich | Zendy

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Halogen Bonding of (Iodoethynyl)benzene Derivatives in Solution

Author(s) -

Oliver Dumele∞,

Dino Wu,

Nils Trapp,

Nancy S. Goroff,

François Diederich

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502099j

Subject(s) - quinuclidine , chemistry , benzene , pyridine , taft equation , halogen bond , halogen , solid state , computational chemistry , crystallography , medicinal chemistry , organic chemistry , substituent , alkyl

Halogen bonding (XB) between (iodoethynyl)benzene donors and quinuclidine in benzene affords binding free enthalpies (ΔG, 298 K) between -1.1 and -2.4 kcal mol(-1), with a strong LFER with the Hammett parameter σpara. The enthalpic driving force is compensated by an unfavorable entropic term. The binding affinity of XB acceptors increases in the order pyridine < C═O < S═O < P═O < quinuclidine. Diverse XB packing motifs are observed in the solid state.

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