Existence of non classical carboanions
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As we know that there are some non classical carbo cations but my question is we know there is an existence of non classical carbocations and their stability is so high then classical Carbo cations but is there any existence of non classical Carboanions. I have not seen non classical carboanions in books. If there is any existence of non classical carboanions then please explain me with example
organic-chemistry
asked 5 hours ago
Saheb Garain great chemist
524
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up vote
5
down vote
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As we know that there are some non classical carbo cations but my question is we know there is an existence of non classical carbocations and their stability is so high then classical Carbo cations but is there any existence of non classical Carboanions. I have not seen non classical carboanions in books. If there is any existence of non classical carboanions then please explain me with example
organic-chemistry
asked 5 hours ago
Saheb Garain great chemist
524
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
5 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
4 hours ago
add a comment |
up vote
5
down vote
favorite
up vote
5
down vote
favorite
As we know that there are some non classical carbo cations but my question is we know there is an existence of non classical carbocations and their stability is so high then classical Carbo cations but is there any existence of non classical Carboanions. I have not seen non classical carboanions in books. If there is any existence of non classical carboanions then please explain me with example
organic-chemistry
asked 5 hours ago
Saheb Garain great chemist
524
As we know that there are some non classical carbo cations but my question is we know there is an existence of non classical carbocations and their stability is so high then classical Carbo cations but is there any existence of non classical Carboanions. I have not seen non classical carboanions in books. If there is any existence of non classical carboanions then please explain me with example
organic-chemistry
organic-chemistry
asked 5 hours ago
Saheb Garain great chemist
524
asked 5 hours ago
Saheb Garain great chemist
524
asked 5 hours ago
Saheb Garain great chemist
524
asked 5 hours ago
Saheb Garain great chemist
524
asked 5 hours ago
Saheb Garain great chemist
524
524
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
5 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
4 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
5 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
4 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
5 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
5 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
4 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
4 hours ago
add a comment |
1 Answer
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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 1 hour ago
Organic Chemistry Explained
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1 Answer
1
active
oldest
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1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
up vote
6
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 1 hour ago
Organic Chemistry Explained
66616
add a comment |
up vote
6
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 1 hour ago
Organic Chemistry Explained
66616
add a comment |
up vote
6
down vote
up vote
6
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 1 hour ago
Organic Chemistry Explained
66616
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 1 hour ago
Organic Chemistry Explained
66616
answered 1 hour ago
Organic Chemistry Explained
66616
answered 1 hour ago
Organic Chemistry Explained
66616
answered 1 hour ago
Organic Chemistry Explained
66616
66616
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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
5 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
4 hours ago