About: Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid

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About: Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Enhanced acidity of sterically hindered carboxylic acids has been explained by steric inhibition to resonance (SIR) and van der Waals (vdW) tension. These two terms have been quantitatively evaluated on a model comparing two isomers, 2-tert-butylbenzoic acid (3) and 4-tert-butylbenzoic acid (4). Energies and geometries of 3 and 4 and their anions have been calculated using the B3LYP model at a 6-31+G(d,p) or 6-311+G(3df,2pd) basis, both in minimum-energy conformations and with a constrained dihedral angle between the ring plane and carboxyl plane. From comparison of the two isomers it follows that SIR contributes significantly to the higher energy of 3, but also raises similarly the energy of its anion 3A. Enhanced acidity of sterically hindered carboxylic acids has been explained by steric inhibition to resonance (SIR) and van der Waals (vdW) tension. These two terms have been quantitatively evaluated on a model comparing two isomers, 2-tert-butylbenzoic acid (3) and 4-tert-butylbenzoic acid (4). Energies and geometries of 3 and 4 and their anions have been calculated using the B3LYP model at a 6-31+G(d,p) or 6-311+G(3df,2pd) basis, both in minimum-energy conformations and with a constrained dihedral angle between the ring plane and carboxyl plane. From comparison of the two isomers it follows that SIR contributes significantly to the higher energy of 3, but also raises similarly the energy of its anion 3A. (en)
Title	Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid (en)
skos:prefLabel	Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid (en)
skos:notation	RIV/60461373:22310/01:00003930!RIV/2004/MSM/223104/N
http://linked.open.../vavai/riv/strany	250-254
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/99/1454), Z(AV0Z4055905), Z(MSM 223100001)
http://linked.open...iv/cisloPeriodika	25
http://linked.open...vai/riv/dodaniDat	2004
http://linked.open...aciTvurceVysledku	Böhm, Stanislav
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	697249
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/01:00003930
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Terc.-butylbenzové kyseliny; slučovací entalpie; isodesmické reakce; resonanční energie; substituční efekt; stérické efekty; ab initio výpočty; DFT. (en)
http://linked.open.../riv/klicoveSlovo	DFT. isodesmické reakce resonanční energie slučovací entalpie substituční efekt ab initio výpočty Terc.-butylbenzové kyseliny stérické efekty
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[2708CFBCE779]
http://linked.open...i/riv/nazevZdroje	New Journal of Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	2 (xsd:int)
http://linked.open...ocetUcastnikuAkce	0 (xsd:int)
http://linked.open...nichUcastnikuAkce	0 (xsd:int)
http://linked.open...vavai/riv/projekt	Thermodynamics of substituent effects in water solution
http://linked.open...UplatneniVysledku	2001
http://linked.open...v/svazekPeriodika	N
http://linked.open...iv/tvurceVysledku	Böhm, Stanislav Exner, Otto
http://linked.open...n/vavai/riv/zamer	Chemical principles of selected biological phenomena in medicine and ecology http://linked.opendata.cz/resource/domain/vavai/zamer/MSM%20223100001
issn	1144-0546
number of pages	5 (xsd:int)
http://localhost/t...ganizacniJednotka	22310

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