Do non-classical carbanions exist?
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There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
edited Dec 23 at 22:51
orthocresol♦
38k7111228
asked Dec 16 at 10:20
Saheb Garain great chemist
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There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
edited Dec 23 at 22:51
orthocresol♦
38k7111228
asked Dec 16 at 10:20
Saheb Garain great chemist
946
If an answer has helped solve your question, please consider upvoting and/or accepting one (by clicking on the tick next to the voting buttons). That's the Stack Exchange way of saying thank you! See also: chemistry.stackexchange.com/help/someone-answers
– orthocresol♦
Dec 24 at 2:26
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There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
edited Dec 23 at 22:51
orthocresol♦
38k7111228
asked Dec 16 at 10:20
Saheb Garain great chemist
946
There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
organic-chemistry ions resonance
edited Dec 23 at 22:51
orthocresol♦
38k7111228
asked Dec 16 at 10:20
Saheb Garain great chemist
946
edited Dec 23 at 22:51
orthocresol♦
38k7111228
asked Dec 16 at 10:20
Saheb Garain great chemist
946
edited Dec 23 at 22:51
orthocresol♦
38k7111228
edited Dec 23 at 22:51
orthocresol♦
38k7111228
edited Dec 23 at 22:51
orthocresol♦
38k7111228
38k7111228
asked Dec 16 at 10:20
Saheb Garain great chemist
946
asked Dec 16 at 10:20
Saheb Garain great chemist
946
asked Dec 16 at 10:20
Saheb Garain great chemist
946
946
If an answer has helped solve your question, please consider upvoting and/or accepting one (by clicking on the tick next to the voting buttons). That's the Stack Exchange way of saying thank you! See also: chemistry.stackexchange.com/help/someone-answers
– orthocresol♦
Dec 24 at 2:26
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If an answer has helped solve your question, please consider upvoting and/or accepting one (by clicking on the tick next to the voting buttons). That's the Stack Exchange way of saying thank you! See also: chemistry.stackexchange.com/help/someone-answers
– orthocresol♦
Dec 24 at 2:26
If an answer has helped solve your question, please consider upvoting and/or accepting one (by clicking on the tick next to the voting buttons). That's the Stack Exchange way of saying thank you! See also: chemistry.stackexchange.com/help/someone-answers
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If an answer has helped solve your question, please consider upvoting and/or accepting one (by clicking on the tick next to the voting buttons). That's the Stack Exchange way of saying thank you! See also: chemistry.stackexchange.com/help/someone-answers
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2 Answers
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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
421211
1
Please give me some references
– Saheb Garain great chemist
Dec 16 at 16:32
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).
edited Dec 24 at 0:34
orthocresol♦
38k7111228
answered Dec 16 at 13:46
Organic Chemistry Explained
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2 Answers
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2 Answers
2
active
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active
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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
421211
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
421211
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
421211
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
421211
edited Dec 16 at 16:57
answered Dec 16 at 16:09
YUSUF HASAN
421211
answered Dec 16 at 16:09
YUSUF HASAN
421211
answered Dec 16 at 16:09
YUSUF HASAN
421211
421211
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 |
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).
edited Dec 24 at 0:34
orthocresol♦
38k7111228
answered Dec 16 at 13:46
Organic Chemistry Explained
77617
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).
edited Dec 24 at 0:34
orthocresol♦
38k7111228
answered Dec 16 at 13:46
Organic Chemistry Explained
77617
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).
edited Dec 24 at 0:34
orthocresol♦
38k7111228
answered Dec 16 at 13:46
Organic Chemistry Explained
77617
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).
edited Dec 24 at 0:34
orthocresol♦
38k7111228
answered Dec 16 at 13:46
Organic Chemistry Explained
77617
edited Dec 24 at 0:34
orthocresol♦
38k7111228
edited Dec 24 at 0:34
orthocresol♦
38k7111228
edited Dec 24 at 0:34
orthocresol♦
38k7111228
38k7111228
answered Dec 16 at 13:46
Organic Chemistry Explained
77617
answered Dec 16 at 13:46
Organic Chemistry Explained
77617
answered Dec 16 at 13:46
Organic Chemistry Explained
77617
77617
add a comment |
add a comment |
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If an answer has helped solve your question, please consider upvoting and/or accepting one (by clicking on the tick next to the voting buttons). That's the Stack Exchange way of saying thank you! See also: chemistry.stackexchange.com/help/someone-answers
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