Is phosphorine (C₅H₅P) aromatic?
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Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
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Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
2
Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23
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up vote
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up vote
10
down vote
favorite
Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
edited Nov 24 at 19:50
Mithoron
3,64382844
3,64382844
asked Nov 23 at 15:34
user137644
1025
1025
2
Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23
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2
Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23
2
2
Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23
Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23
add a comment |
1 Answer
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13
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Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン♦
Dec 4 at 16:38
So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン♦
Dec 5 at 9:22
add a comment |
1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
up vote
13
down vote
accepted
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン♦
Dec 4 at 16:38
So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン♦
Dec 5 at 9:22
add a comment |
up vote
13
down vote
accepted
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン♦
Dec 4 at 16:38
So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン♦
Dec 5 at 9:22
add a comment |
up vote
13
down vote
accepted
up vote
13
down vote
accepted
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
edited Nov 24 at 21:15
Waylander
5,2761719
5,2761719
answered Nov 23 at 16:26
Oscar Lanzi
14.3k12546
14.3k12546
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン♦
Dec 4 at 16:38
So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン♦
Dec 5 at 9:22
add a comment |
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン♦
Dec 4 at 16:38
So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン♦
Dec 5 at 9:22
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン♦
Dec 4 at 16:38
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン♦
Dec 4 at 16:38
So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38
So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン♦
Dec 5 at 9:22
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン♦
Dec 5 at 9:22
add a comment |
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2
Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23