J. Phys. Org. Chem.
 1998
DOI: 10.1002/(sici)1099-1395(199808/09)11:8/9<663::aid-poc55>3.0.co;2-x
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Absolute proton affinities of some substituted toluenes: the additivity rule of thumb foripso attack

Mirjana Eckert-Maksi
1
,
Andrea Kne evi
2
,
Zvonimir B. Maksi
3
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Cited by 8 publications

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“…Ipso -protonation at C4 in isomer f is less favorable than protonation at C2 in g by 6.8 kJ/mol, whereas the meta -tautomer h is energetically highly unfavorable (115.6 kJ/mol) due to the lack of mesomeric stabilization by the dimethylamino substituent. The relative stabilities of the para -toluidinium tautomers f , g , and h are in agreement with the well-established local proton affinities of substituted benzenium ions and the additivity rule of the substituent effects. − In fact, ring -protonated N , N -dialkylanilinium ions are known to be the kinetic products of protonation, whereas the N -protonated tautomers are the favored thermodynamic products. The former ion structures were mainly observed in chemical ionization (CI)-MS gas-phase experiments …”
Section: Resultssupporting
confidence: 78%
Exaggerated anticipatory anxiety is common in social anxiety disorder (SAD). Neuroimaging studies have revealed altered neural activity in response to social stimuli in SAD, but fewer studies have examined neural activity during anticipation of feared social stimuli in SAD. The current study examined the time course and magnitude of activity in threat processing brain regions during speech anticipation in socially anxious individuals and healthy controls (HC). Method Participants (SAD n = 58; HC n = 16) underwent functional magnetic resonance imaging (fMRI) during which they completed a 90s control anticipation task and 90s speech anticipation task.
“…Ipso -protonation at C4 in isomer f is less favorable than protonation at C2 in g by 6.8 kJ/mol, whereas the meta -tautomer h is energetically highly unfavorable (115.6 kJ/mol) due to the lack of mesomeric stabilization by the dimethylamino substituent. The relative stabilities of the para -toluidinium tautomers f , g , and h are in agreement with the well-established local proton affinities of substituted benzenium ions and the additivity rule of the substituent effects. − In fact, ring -protonated N , N -dialkylanilinium ions are known to be the kinetic products of protonation, whereas the N -protonated tautomers are the favored thermodynamic products. The former ion structures were mainly observed in chemical ionization (CI)-MS gas-phase experiments …”
Section: Resultssupporting
confidence: 78%
Exaggerated anticipatory anxiety is common in social anxiety disorder (SAD). Neuroimaging studies have revealed altered neural activity in response to social stimuli in SAD, but fewer studies have examined neural activity during anticipation of feared social stimuli in SAD. The current study examined the time course and magnitude of activity in threat processing brain regions during speech anticipation in socially anxious individuals and healthy controls (HC). Method Participants (SAD n = 58; HC n = 16) underwent functional magnetic resonance imaging (fMRI) during which they completed a 90s control anticipation task and 90s speech anticipation task.
Exaggerated anticipatory anxiety is common in social anxiety disorder (SAD). Neuroimaging studies have revealed altered neural activity in response to social stimuli in SAD, but fewer studies have examined neural activity during anticipation of feared social stimuli in SAD. The current study examined the time course and magnitude of activity in threat processing brain regions during speech anticipation in socially anxious individuals and healthy controls (HC). Method Participants (SAD n = 58; HC n = 16) underwent functional magnetic resonance imaging (fMRI) during which they completed a 90s control anticipation task and 90s speech anticipation task.
Exaggerated anticipatory anxiety is common in social anxiety disorder (SAD). Neuroimaging studies have revealed altered neural activity in response to social stimuli in SAD, but fewer studies have examined neural activity during anticipation of feared social stimuli in SAD. The current study examined the time course and magnitude of activity in threat processing brain regions during speech anticipation in socially anxious individuals and healthy controls (HC). Method Participants (SAD n = 58; HC n = 16) underwent functional magnetic resonance imaging (fMRI) during which they completed a 90s control anticipation task and 90s speech anticipation task.
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