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
edited Nov 24 '18 at 19:50
Mithoron
3,70882846
asked Nov 23 '18 at 15:34
user137644user137644
995
$endgroup$
add a comment |
$begingroup$
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
edited Nov 24 '18 at 19:50
Mithoron
3,70882846
asked Nov 23 '18 at 15:34
user137644user137644
995
$endgroup$
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
add a comment |
$begingroup$
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
edited Nov 24 '18 at 19:50
Mithoron
3,70882846
asked Nov 23 '18 at 15:34
user137644user137644
995
$endgroup$
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 '18 at 19:50
Mithoron
3,70882846
asked Nov 23 '18 at 15:34
user137644user137644
995
edited Nov 24 '18 at 19:50
Mithoron
3,70882846
asked Nov 23 '18 at 15:34
user137644user137644
995
edited Nov 24 '18 at 19:50
Mithoron
3,70882846
edited Nov 24 '18 at 19:50
Mithoron
3,70882846
edited Nov 24 '18 at 19:50
Mithoron
3,70882846
3,70882846
asked Nov 23 '18 at 15:34
user137644user137644
995
asked Nov 23 '18 at 15:34
user137644user137644
995
asked Nov 23 '18 at 15:34
user137644user137644
995
995
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
add a comment |
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
3
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
add a comment |
1 Answer
1
active
oldest
votes
$begingroup$
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 '18 at 21:15
Waylander
6,73411424
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
$endgroup$
1
$begingroup$
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.
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– Martin - マーチン♦
Dec 4 '18 at 16:38
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So ... you apparently think this is not aromatic?
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– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
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1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
$begingroup$
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 '18 at 21:15
Waylander
6,73411424
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
$endgroup$
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
$begingroup$
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 '18 at 21:15
Waylander
6,73411424
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
$endgroup$
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
$begingroup$
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 '18 at 21:15
Waylander
6,73411424
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
$endgroup$
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 '18 at 21:15
Waylander
6,73411424
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
edited Nov 24 '18 at 21:15
Waylander
6,73411424
edited Nov 24 '18 at 21:15
Waylander
6,73411424
edited Nov 24 '18 at 21:15
Waylander
6,73411424
6,73411424
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
16.2k12749
16.2k12749
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
1
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
1
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
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3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23