Existence of non-classical carbanions
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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 1 hour ago
Jan
48.6k7114256
asked 7 hours ago
Saheb Garain great chemist
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add a comment |
up vote
9
down vote
favorite
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 1 hour ago
Jan
48.6k7114256
asked 7 hours ago
Saheb Garain great chemist
724
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
7 hours ago
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
7 hours ago
add a comment |
up vote
9
down vote
favorite
up vote
9
down vote
favorite
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 1 hour ago
Jan
48.6k7114256
asked 7 hours ago
Saheb Garain great chemist
724
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 1 hour ago
Jan
48.6k7114256
asked 7 hours ago
Saheb Garain great chemist
724
edited 1 hour ago
Jan
48.6k7114256
asked 7 hours ago
Saheb Garain great chemist
724
edited 1 hour ago
Jan
48.6k7114256
edited 1 hour ago
Jan
48.6k7114256
edited 1 hour ago
Jan
48.6k7114256
48.6k7114256
asked 7 hours ago
Saheb Garain great chemist
724
asked 7 hours ago
Saheb Garain great chemist
724
asked 7 hours ago
Saheb Garain great chemist
724
724
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
7 hours ago
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
7 hours ago
add a comment |
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
7 hours ago
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
7 hours ago
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
7 hours ago
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
7 hours ago
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
7 hours ago
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
7 hours ago
add a comment |
2 Answers
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up vote
9
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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 4 hours ago
Organic Chemistry Explained
69616
add a comment |
up vote
3
down vote
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered 2 hours ago
YUSUF HASAN
314211
Please give me some references
– Saheb Garain great chemist
1 hour ago
add a comment |
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2 Answers
2
active
oldest
votes
2 Answers
2
active
oldest
votes
active
oldest
votes
active
oldest
votes
up vote
9
down vote
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 4 hours ago
Organic Chemistry Explained
69616
add a comment |
up vote
9
down vote
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 4 hours ago
Organic Chemistry Explained
69616
add a comment |
up vote
9
down vote
up vote
9
down vote
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 4 hours ago
Organic Chemistry Explained
69616
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 4 hours ago
Organic Chemistry Explained
69616
answered 4 hours ago
Organic Chemistry Explained
69616
answered 4 hours ago
Organic Chemistry Explained
69616
answered 4 hours ago
Organic Chemistry Explained
69616
69616
add a comment |
add a comment |
up vote
3
down vote
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered 2 hours ago
YUSUF HASAN
314211
Please give me some references
– Saheb Garain great chemist
1 hour ago
add a comment |
up vote
3
down vote
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered 2 hours ago
YUSUF HASAN
314211
Please give me some references
– Saheb Garain great chemist
1 hour ago
add a comment |
up vote
3
down vote
up vote
3
down vote
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered 2 hours ago
YUSUF HASAN
314211
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered 2 hours ago
YUSUF HASAN
314211
edited 1 hour ago
answered 2 hours ago
YUSUF HASAN
314211
answered 2 hours ago
YUSUF HASAN
314211
answered 2 hours ago
YUSUF HASAN
314211
314211
Please give me some references
– Saheb Garain great chemist
1 hour ago
add a comment |
Please give me some references
– Saheb Garain great chemist
1 hour ago
Please give me some references
– Saheb Garain great chemist
1 hour ago
Please give me some references
– Saheb Garain great chemist
1 hour ago
add a comment |
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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
7 hours ago
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
7 hours ago