For this purpose, 6.2 eq of [Msim]Cl and 2 eq of NaNO2 were reacted with 1 eq of p-methoxyphenol. >> They involve the formation of (i) the nitronium ion 24 or (ii) the nitrogen dioxide radical. The major isomer is para and hence, its pathway has to be the lowest in energy. Nitration takes place almost exclusively on ortho-para positions. This means that the ortho and para benzenonium ions must be much less unstable that the meta one. 0000001109 00000 n The positive charge delocalizes along the ortho and para positions. 2) Relative reaction rate 0000003893 00000 n Phenol reacts 1000 times faster than benzene. << Selective and eco-friendly nitration of phenols. /Type/Encoding In another study, the [Msim]Cl/NaNO2 system was examined for di-nitration of phenols. (�� ? (�� Nitration of phenol as a special case has been studied using various nitrating agents under different conditions [4-22]. (�� 11 0 obj << << /Resources<< 0000001646 00000 n 0000003277 00000 n << Two different mechanisms have been proposed for the nitration of tyrosine. $4�%�&'()*56789:CDEFGHIJSTUVWXYZcdefghijstuvwxyz�������������������������������������������������������������������������� ? 0000002719 00000 n The energy diagram of phenol nitration is qualitatively similar to benzene's. (�� /ColorSpace/DeviceRGB (�� Therefore, the para position reacts 58/20 times as fast as the ortho, i.e. (�� 0000004558 00000 n /ExtGState 11 0 R This means that the ortho and para benzenonium ions must be much less unstable that the meta one. Nitration takes place almost exclusively on ortho-para positions. endstream (�� >> 0000002321 00000 n (�� Phenol reacts faster than benzene. This means that the ortho and para benzenonium ions must be much less unstable that the meta one. 14 0 obj (�� 2.9:1. /ProcSet[/PDF/ImageC] Mechanism of Tyrosine Nitration. trailer << /Size 58 /Info 37 0 R /Root 40 0 R /Prev 34943 /ID[] >> startxref 0 %%EOF 40 0 obj << /Type /Catalog /Pages 38 0 R /Outlines 24 0 R /OpenAction [ 41 0 R /XYZ null null null ] /PageMode /UseNone >> endobj 56 0 obj << /S 140 /O 197 /Filter /FlateDecode /Length 57 0 R >> stream /Subtype/Form /Matrix[1 0 0 1 0 0] Entry Substrates Products Time(h) Yields(%)a 1 Phenol o-nitro phenol 6 75 2 4-nitro phenol 2,4-dinitro phenol 6 98 3 4-bromo phenol Reaction: Phenol + HNO3 --> 2-nitrophenol + 4-nitrophenol. %&'()*456789:CDEFGHIJSTUVWXYZcdefghijstuvwxyz��������������������������������������������������������������������������� Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol. The oxygen is thus able to further delocalize the positive charge by sharing its electron lone pairs. Also, nitro compounds find use in many industrial applications [2-4]. $, !$4.763.22:ASF:=N>22HbINVX]^]8EfmeZlS[]Y�� C**Y;2;YYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYY�� k�" �� p� (���j���U��K����6��Z�.�x���4���K̲t����&�Q�+�����6�V*�� ��? 0000007065 00000 n 0000000727 00000 n 0000003468 00000 n b) and why is 3-nitrophenol not present in products (in any signifigant amount) (is this due to resonance?) 0000001477 00000 n 0000001311 00000 n /R5 14 0 R The intermediate bezenonium ion is more stable when the OH is attached to it. >> (�� endobj 39 0 obj << /Linearized 1 /O 41 /H [ 864 266 ] /L 35851 /E 7294 /N 7 /T 34953 >> endobj xref 39 19 0000000016 00000 n :�VZ���Z�4����!��Rl�˂s���^X�c�4��*���WQ+F��Y�AEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPEPE� ���k1�оXn�&���cl�7ϊ�}kY�Q�pI�@���j ��\�N�H �R$ay��������_��J���/�z��vtZ���C}*z���C}(��Q� !�b��G���� �E����r��O��H��,s7�5��Wiw��Ҽ��`�NG5��_ď��v� z�V��+���l�U�QE QE QE QE QE QE QE QE QE QE QE QE QE QE QE QE QE QE QE QE QI@c��zt-��[�a��o���y>��K�\0$����y���� -g"�e��$ay�O�aQ���RTo��P�x�=Gһ:�� ��]���� P�J���� P�J �� �E����v��S� !��B}�;�Q�u`ќb���:�x��$H�~��Ӭn��"�9�+�u�+�� )I��@�EV����%h�r*� Phenol reacts 1000 times faster than benzene. a) What is the reaction mechanism for this reaction? �� � w !1AQaq"2�B���� #3R�br� endobj 25 The formation of nitronium ion from peroxynitrite is favored over the formation of nitrogen dioxide radical in the presence of protein bound or free metal ions. Therefore, the resonance hybrid is described with only three resonance forms and is more unstable than the preceding cases. The resonace forms of each ion give us the answer. The intermediate bezenonium ion is more stable when the OH is attached to it. x�+T0�3T0 A(��˥d��^�U�`dhn�g6�47�32t ��������T�%�+K�J (�� Nitration takes place almost exclusively on ortho-para positions. c) and could there be any other biproducts in this reaction. �� � } !1AQa"q2���#B��R��$3br� ��(�� �� ֊�����=C����>����_��J�������T�����P����B-���������ֲ��1�QMc�� ꍃ�C�S��/� u�+�:�+�s^�ev�p,���W�2�m�z���QU��"��^3���@��(��(��(��(��(��(��(��(��(��(��(��(��(��(��(��(��(��}sY�N���8�[�a��`O�^M�k3_��W4 kZ����*����h��4�Q����� �4. /BitsPerComponent 8 /Metadata 15 0 R /Name/Im1 /XObject 12 0 R 0000001817 00000 n 7 0 obj (�� We have to take out this statistical factor in order to compare true rate ratios. /FormType 1 stream 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 … >> (�� The reasoning is similar to that used for the ortho position. 3) Direction of substitution. H�b```�>9���1� g�ǹ�"�"z +:z@Tpj;w�6�,�I��{D���`aH�((� �k@2�f`�y���Xl��@[@��C��+� �B�+v2,�b�P��p� �Q�@����u*@� !�& endstream endobj 57 0 obj 153 endobj 41 0 obj << /Type /Page /Parent 38 0 R /Resources 44 0 R /Contents 54 0 R /Annots [ 42 0 R 43 0 R ] /MediaBox [ 0 0 595 842 ] /CropBox [ 0 0 595 842 ] /Rotate 0 >> endobj 42 0 obj << /A << /S /URI /URI (http://www.mdpi.org/)>> /Type /Annot /Subtype /Link /Rect [ 437 679 540 693 ] /C [ 0 0 0 ] /Border [ 0 0 0 ] /H /I >> endobj 43 0 obj << /A << /S /URI /URI (mailto:Zolfi@basu.ac.ir)>> /Type /Annot /Subtype /Link /Rect [ 364 497 446 511 ] /C [ 0 0 0 ] /Border [ 0 0 0 ] /H /I >> endobj 44 0 obj << /ProcSet [ /PDF /Text ] /Font << /TT2 48 0 R /TT4 45 0 R /TT6 52 0 R /TT8 51 0 R >> /ExtGState << /GS1 55 0 R >> /ColorSpace << /Cs5 50 0 R >> >> endobj 45 0 obj << /Type /Font /Subtype /TrueType /FirstChar 32 /LastChar 122 /Widths [ 250 0 0 0 0 1000 0 0 333 333 500 0 250 333 250 278 500 500 500 500 500 500 500 500 500 500 333 0 0 0 0 0 0 722 0 722 722 667 0 778 778 389 0 778 0 944 722 778 611 0 722 556 667 722 0 0 722 722 667 333 0 333 0 0 0 500 556 444 556 444 333 500 556 278 333 556 278 833 556 500 556 0 444 389 333 556 0 722 500 500 444 ] /Encoding /WinAnsiEncoding /BaseFont /TimesNewRomanPS-BoldMT /FontDescriptor 46 0 R >> endobj 46 0 obj << /Type /FontDescriptor /Ascent 891 /CapHeight 0 /Descent -216 /Flags 34 /FontBBox [ -184 -307 1089 1026 ] /FontName /TimesNewRomanPS-BoldMT /ItalicAngle 0 /StemV 133 >> endobj 47 0 obj << /Type /FontDescriptor /Ascent 891 /CapHeight 0 /Descent -216 /Flags 98 /FontBBox [ -189 -307 1120 1023 ] /FontName /TimesNewRomanPS-ItalicMT /ItalicAngle -15 /StemV 0 >> endobj 48 0 obj << /Type /Font /Subtype /TrueType /FirstChar 32 /LastChar 148 /Widths [ 250 0 0 0 0 0 778 0 333 333 0 0 250 333 250 278 500 500 500 500 500 500 500 500 500 500 333 333 0 0 0 0 0 611 611 667 722 611 0 722 722 333 444 0 556 833 667 722 611 0 611 500 556 0 611 0 0 0 0 0 0 0 0 0 0 500 500 444 500 444 278 500 500 278 0 444 278 722 500 500 500 500 389 389 278 500 444 667 444 444 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 333 556 556 ] /Encoding /WinAnsiEncoding /BaseFont /TimesNewRomanPS-ItalicMT /FontDescriptor 47 0 R >> endobj 49 0 obj << /Type /FontDescriptor /Ascent 891 /CapHeight 0 /Descent -216 /Flags 34 /FontBBox [ -167 -307 1009 1007 ] /FontName /TimesNewRomanPSMT /ItalicAngle 0 /StemV 0 >> endobj 50 0 obj [ /CalRGB << /WhitePoint [ 0.9505 1 1.089 ] /Gamma [ 2.22221 2.22221 2.22221 ] /Matrix [ 0.4124 0.2126 0.0193 0.3576 0.71519 0.1192 0.1805 0.0722 0.9505 ] >> ] endobj 51 0 obj << /Type /Font /Subtype /TrueType /FirstChar 99 /LastChar 117 /Widths [ 444 0 444 0 0 0 0 0 0 278 778 0 500 0 0 0 389 0 556 ] /Encoding /WinAnsiEncoding /BaseFont /TimesNewRomanPS-BoldItalicMT /FontDescriptor 53 0 R >> endobj 52 0 obj << /Type /Font /Subtype /TrueType /FirstChar 32 /LastChar 183 /Widths [ 250 0 408 0 0 833 778 0 333 333 500 564 250 333 250 278 500 500 500 500 500 500 500 500 500 500 278 278 0 0 0 0 921 722 667 667 722 611 556 722 722 333 389 722 611 889 722 722 556 722 667 556 611 722 722 944 722 722 611 333 0 333 0 0 0 444 500 444 500 444 333 500 500 278 278 500 278 778 500 500 500 500 333 389 278 500 500 722 500 500 444 480 0 480 541 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 333 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 760 0 0 0 0 0 0 400 0 0 0 0 0 0 250 ] /Encoding /WinAnsiEncoding /BaseFont /TimesNewRomanPSMT /FontDescriptor 49 0 R >> endobj 53 0 obj << /Type /FontDescriptor /Ascent 891 /CapHeight 0 /Descent -216 /Flags 98 /FontBBox [ -184 -307 1206 1032 ] /FontName /TimesNewRomanPS-BoldItalicMT /ItalicAngle -15 /StemV 133 >> endobj 54 0 obj << /Length 2226 /Filter /FlateDecode >> stream

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