Binding of cyclic carboxylates to octa-acid deep-cavity cavitand

Journal of Computer-Aided Molecular Design

Volumn 28, Issue 4, 2014, Pages 319-325

  Gibb, Corinne L D ^a   Gibb, Bruce C ^a  

^a Tulane University   (United States)

Author keywords

Host guest chemistry; Hydrophobic effect; Supramolecular chemistry; Water

Indexed keywords

BINDING ENERGY; CARBOXYLATION; FREE ENERGY; HYDROPHOBICITY; SOLUTIONS;

ASSOCIATION CONSTANT; CAVITANDS; CYCLIC CARBOXYLATES; DEEP CAVITY; FREE-ENERGY DIFFERENCE; HOSTGUEST CHEMISTRY; HYDROPHOBIC EFFECT; ISOTHERMAL TITRATION CALORIMETRY; NMR TITRATION; STATISTICAL ASSESSMENT;

SUPRAMOLECULAR CHEMISTRY;

ACID; BENZOIC ACID; BORATE SODIUM; CARBOXYLIC ACID; 4-ETHYLBENZOIC ACID; BENZOIC ACID DERIVATIVE; CAVITAND; ETHER DERIVATIVE; RESORCINOL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; COMPLEX FORMATION; COMPUTER MODEL; COMPUTER PREDICTION; ISOTHERMAL TITRATION CALORIMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; THERMODYNAMICS;

BENZOATES; BINDING SITES; CARBOXYLIC ACIDS; CYCLIZATION; ETHERS, CYCLIC; MODELS, MOLECULAR; RESORCINOLS; THERMODYNAMICS;

EID: 84902831983     PISSN: 0920654X     EISSN: 15734951     Source Type: Journal    
DOI: 10.1007/s10822-013-9690-2     Document Type: Article

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19. Molecular surface areas, volumes, and dipole moments were calculated using MNDO semi empirical calculations following MMFF molecular mechanics conformer searches. The limited conformational flexibility and high symmetry of the different guests suggest accurate dipole moment calculations using this approach
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22. The exchange between the free and bound state is very close to the NMR timescale in the case of 7. Thus, although a 2:1 hostguest ratio gave guest signals indicative of slow exchange, this was only because they undergo relatively large shifts from the free state. In contrast, because the host signals undergo only small shifts upon complexation, these signals appeared to undergo fast exchange. As a result, instead of observing both free and complexed host signals, only a time-averaged signal for each proton type was observed (Fig. 3b)
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