The N-methylquinolinium ion forms a noncovalent complex with molecule A in water that has a standard free

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The N-methylquinolinium ion forms a noncovalent complex with molecule A in water that has a standard free energy of dissociation ΔG°d 5 28.9 kJ mol–1 (6.9 kcal mol–1). The neutral molecule 4-methylquinoline forms a noncovalent complex with molecule A in water with ΔG°d 5 22.2 kJ mol1 (5.3 kcal mol1).

(a) Calculate the dissociation constant for each complex.

(b) Suggest a reason that the binding of the ion to A is stronger than the binding of the neutral molecule to A.

(c) The N-methylquinolinium ion forms a noncovalent complex with molecule B with ΔG°d = 35.2 kJ mol–1 (8.4 kcal mol–1). Suggest a reason that the complex with molecule B has a smaller dissociation constant than the complex with molecule A.- HO HO HO HO A Figure P15.60 CH3 OH - - OH - - N-methylquinolinium ion -- -- || CH3 4-methylquinoline

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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