nitration of phenol mechanism

Two different mechanisms have been proposed for the nitration of tyrosine. The energy diagram of phenol nitration is qualitatively similar to benzene's. G3(MP2)//B3-CEP theory was applied to study the mechanism of phenol nitration in the gas phase, as promoted by the electrophile NO2 (+). /Length 65 >> For this purpose, 6.2 eq of [Msim]Cl and 2 eq of NaNO2 were reacted with 1 eq of p-methoxyphenol.
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%PDF-1.2 %���� widen by nitration of naphtol to give mono-nitrated in high yields (Table 1). (�� The major isomer is para and hence, its pathway has to be the lowest in energy. Selective and eco-friendly nitration of phenols. 0000000864 00000 n a) What is the reaction mechanism for this reaction? 0000004764 00000 n

p� (�� 3) Direction of substitution

/XObject 12 0 R (�� Nitration of phenol by a electrophile substitution? /ColorSpace/DeviceRGB The resonace forms of each ion give us the answer. 11 0 obj 0000003648 00000 n

>> US3519693A US509629A US3519693DA US3519693A US 3519693 A US3519693 A US 3519693A US 509629 A US509629 A US 509629A US 3519693D A US3519693D A US 3519693DA US 3519693 A US3519693 A US 3519693A Authority US United States Prior art keywords phenol reaction solution acid added Prior art date 1965-11-24 Legal status (The legal status is an assumption and is not a legal … >> /Filter/DCTDecode (�� The intermediate bezenonium ion is more stable when the OH is attached to it. (�� 0000002719 00000 n

The OH group activates the aromatic ring in SEAr and lowers the activation energy.

/BitsPerComponent 8 With concentrated nitric acid. (�����f=:;�qI��0�۰��ד�:̷�v��Z�ڍ���i��\��"Fg�I@Ģ�\ With concentrated nitric acid, more nitro groups substitute around the ring to give 2,4,6-trinitrophenol (old name: picric acid). Nitration takes place almost exclusively on ortho-para positions.

2) Relative reaction rate

(�� The oxygen is thus able to further delocalize the positive charge by sharing its electron lone pairs. 0000003468 00000 n 14 0 obj
Also, nitro compounds find use in many industrial applications [2-4].

The OH group activates the aromatic ring in SEAr and lowers the activation energy.

The results of studying this mechanism at the G3(MP2)//B3-CEP level pointed to the occurrence of a The positive charge delocalizes along the ortho and para positions. $, !$4.763.22:ASF:=N>22HbINVX]^]8EfmeZlS[]Y�� C**Y;2;YYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYY�� k�" �� This means that the ortho and para benzenonium ions must be much less unstable that the meta one. ��(�� 0000001130 00000 n In the third resonance form the positive charge lies on the carbon supporting the OH group. 0000003277 00000 n 12 0 obj NH4NO3 +KHSO NH4 4 + +KSO 4 + - HNO 3 +KHSO 4NO 2 + +H2O KSO + - HNO 3 Scheme 2 Table 1. mechanism for the nitration of phenols [33], the follow-ing reported nitrous acid catalyzed mechanism may be approved (Figure 5) [19,34]. endobj stream The electron lone pairs of oxygen delocalizes towards the ring and increases electron density at ortho and para positions. 0000007065 00000 n Phenol reacts 1000 times faster than benzene. /Name/Im1 (���j���U��K����6��Z�.�x���4���K̲t����&�Q�+�����6�V*�� ��?

/Resources<< The reasoning is similar to that used for the ortho position. This means that the ortho and para benzenonium ions must be much less unstable that the meta one.

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