Existence of non-classical carbanions
We know that there are some non-classical carbocations. But have non-classical carbanions also been described? I have not seen non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples
organic-chemistry ions
edited Dec 16 at 16:21
Jan
48.7k7114256
asked Dec 16 at 10:20
Saheb Garain great chemist
875
add a comment |
We know that there are some non-classical carbocations. But have non-classical carbanions also been described? I have not seen non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples
organic-chemistry ions
edited Dec 16 at 16:21
Jan
48.7k7114256
asked Dec 16 at 10:20
Saheb Garain great chemist
875
1
What do you mean by"non classical carbanions"? Non classical carbocations are stabilised by resonance via sigma bonds to empty orbitals, while carbanions are destabilized by +H effect.
– YUSUF HASAN
Dec 16 at 10:44
I mean to say that as nonclassical carbo cations are stabilized by the pi bond shifting which present in homo alylic or homo benzylic positions or they stabilized by sigma bond shifting, now I want to know that the type of stabilization which present in non classical carbo cations is it present in non classical Carbo anions, if they exist.
– Saheb Garain great chemist
Dec 16 at 10:54
add a comment |
We know that there are some non-classical carbocations. But have non-classical carbanions also been described? I have not seen non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples
organic-chemistry ions
edited Dec 16 at 16:21
Jan
48.7k7114256
asked Dec 16 at 10:20
Saheb Garain great chemist
875
We know that there are some non-classical carbocations. But have non-classical carbanions also been described? I have not seen non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples
organic-chemistry ions
organic-chemistry ions
edited Dec 16 at 16:21
Jan
48.7k7114256
asked Dec 16 at 10:20
Saheb Garain great chemist
875
edited Dec 16 at 16:21
Jan
48.7k7114256
asked Dec 16 at 10:20
Saheb Garain great chemist
875
edited Dec 16 at 16:21
Jan
48.7k7114256
edited Dec 16 at 16:21
Jan
48.7k7114256
edited Dec 16 at 16:21
Jan
48.7k7114256
48.7k7114256
asked Dec 16 at 10:20
Saheb Garain great chemist
875
asked Dec 16 at 10:20
Saheb Garain great chemist
875
asked Dec 16 at 10:20
Saheb Garain great chemist
875
875
1
What do you mean by"non classical carbanions"? Non classical carbocations are stabilised by resonance via sigma bonds to empty orbitals, while carbanions are destabilized by +H effect.
– YUSUF HASAN
Dec 16 at 10:44
I mean to say that as nonclassical carbo cations are stabilized by the pi bond shifting which present in homo alylic or homo benzylic positions or they stabilized by sigma bond shifting, now I want to know that the type of stabilization which present in non classical carbo cations is it present in non classical Carbo anions, if they exist.
– Saheb Garain great chemist
Dec 16 at 10:54
add a comment |
1
What do you mean by"non classical carbanions"? Non classical carbocations are stabilised by resonance via sigma bonds to empty orbitals, while carbanions are destabilized by +H effect.
– YUSUF HASAN
Dec 16 at 10:44
I mean to say that as nonclassical carbo cations are stabilized by the pi bond shifting which present in homo alylic or homo benzylic positions or they stabilized by sigma bond shifting, now I want to know that the type of stabilization which present in non classical carbo cations is it present in non classical Carbo anions, if they exist.
– Saheb Garain great chemist
Dec 16 at 10:54
1
1
What do you mean by"non classical carbanions"? Non classical carbocations are stabilised by resonance via sigma bonds to empty orbitals, while carbanions are destabilized by +H effect.
– YUSUF HASAN
Dec 16 at 10:44
What do you mean by"non classical carbanions"? Non classical carbocations are stabilised by resonance via sigma bonds to empty orbitals, while carbanions are destabilized by +H effect.
– YUSUF HASAN
Dec 16 at 10:44
I mean to say that as nonclassical carbo cations are stabilized by the pi bond shifting which present in homo alylic or homo benzylic positions or they stabilized by sigma bond shifting, now I want to know that the type of stabilization which present in non classical carbo cations is it present in non classical Carbo anions, if they exist.
– Saheb Garain great chemist
Dec 16 at 10:54
I mean to say that as nonclassical carbo cations are stabilized by the pi bond shifting which present in homo alylic or homo benzylic positions or they stabilized by sigma bond shifting, now I want to know that the type of stabilization which present in non classical carbo cations is it present in non classical Carbo anions, if they exist.
– Saheb Garain great chemist
Dec 16 at 10:54
add a comment |
2 Answers
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Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz(Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376-377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species.(Brown, J. M. Aust. J. Chem. 2014, 67, 1296-1300)
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
add a comment |
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 at 16:09
YUSUF HASAN
379211
1
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
add a comment |
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2 Answers
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2 Answers
2
active
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Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz(Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376-377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species.(Brown, J. M. Aust. J. Chem. 2014, 67, 1296-1300)
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
add a comment |
Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz(Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376-377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species.(Brown, J. M. Aust. J. Chem. 2014, 67, 1296-1300)
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
add a comment |
Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz(Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376-377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species.(Brown, J. M. Aust. J. Chem. 2014, 67, 1296-1300)
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz(Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376-377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species.(Brown, J. M. Aust. J. Chem. 2014, 67, 1296-1300)
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
answered Dec 16 at 13:46
Organic Chemistry Explained
74617
74617
add a comment |
add a comment |
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 at 16:09
YUSUF HASAN
379211
1
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
add a comment |
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 at 16:09
YUSUF HASAN
379211
1
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
add a comment |
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 at 16:09
YUSUF HASAN
379211
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 at 16:09
YUSUF HASAN
379211
edited Dec 16 at 16:57
answered Dec 16 at 16:09
YUSUF HASAN
379211
answered Dec 16 at 16:09
YUSUF HASAN
379211
answered Dec 16 at 16:09
YUSUF HASAN
379211
379211
1
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
add a comment |
1
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
1
1
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
add a comment |
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1
What do you mean by"non classical carbanions"? Non classical carbocations are stabilised by resonance via sigma bonds to empty orbitals, while carbanions are destabilized by +H effect.
– YUSUF HASAN
Dec 16 at 10:44
I mean to say that as nonclassical carbo cations are stabilized by the pi bond shifting which present in homo alylic or homo benzylic positions or they stabilized by sigma bond shifting, now I want to know that the type of stabilization which present in non classical carbo cations is it present in non classical Carbo anions, if they exist.
– Saheb Garain great chemist
Dec 16 at 10:54