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___________________________________________________RESULTADOS E DISCUSSÃOligada diretamente ao anel aromático na posição 2 apresentou-se como umsingleto em 2,21 ppm (Figura 58, Anexo 134).AOHOHBOHCOHFigura 57. A. Cromatograma de íons totais (CG-EM, 70 eV) da secreção dedefesa de H. mexicanus; B. Espectro de massas do 2,5-dimetil-fenol; C.Espectro de massas do 2-metil-5-etil-fenol.117
___________________________________________________RESULTADOS E DISCUSSÃOJá o 2,5-dimetil-fenol apresentou sinais de maior abundância, com umsingleto em 6,60 ppm, um dubleto com acoplamento orto em 7,03 ppm (J 7,63Hz) e um dubleto com acoplamento orto em 6,66 ppm (J 7,63 Hz). A metilaligada na posição 2 do anel aromático apareceu em 2,20 ppm, enquanto que ametila na posição 5 apresentou-se mais desblindada, em 2,27 ppm (Figura 58,Anexo 134).A confirmação das posições dos substituintes no anel aromático foirealizada através da análise do espectro de RMN de 1 H NOESY 2D. Asprincipais correlações são mostradas na Figura 54 (Anexo 136). Finalmente, airradiação dos sinais dos hidrogênios metilênicos em 2,56 ppm do 2-metil-5-etil-fenol no experimento de diferença de NOE resultou em incrementos nossinais dos hidrogênios em 6,63 (0,1 %), 6,69 (0,12 %) e 1,2 ppm (0,15 %),mostrando definitivamente que o substituinte etila ocupa a posição 5 no anelaromático (Anexo 135).A1,20 ppm(q, J = 7,63 Hz)6,63 ppm (s)2,56 ppm(q, J = 7,63 Hz)4,80 ppm (largo) 4,80 ppm (largo)OHOH2,21 ppm (s)6,60 ppm (s)2,20 ppm (s)7,00 ppm (d, J = 7,62 Hz)6,69 ppm (d, J = 7,62 Hz)2,27 ppm(s)7,03 ppm (d, J = 7,636,66 ppm (d, J = 7,63 Hz)BOH OH COH0,10 %0,15 %0,12 %Figura 58. A. Deslocamentos químicos de RMN de 1 H das substâncias de defesaproduzidas por H. mexicanus. B. Principais correlações de RMN de 1 H NOESY 2D.C. Incrementos de NOE (RMN de 1 H NOESY 1D) observados no 2-metil-5-etil-fenolapós irradiação seletiva do sinal dos hidrogênios metilênicos em 2,56 ppm.118
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VDEDICATÓRIADEDICO ESTE TRABALHO
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VIIIBraga, Dr. José Augusto R. Rod
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XPOMINI, A. M. ; CABEÇA, L. F. ; C
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XIIde cadeia longa. Realizou-se tam
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XIVacyl-HSLs. We have also studied
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XVINBNOEODPpmR fRMNROERLUSTDSAMTMST
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XVIII3.3.4.2. Síntese da (S)-N-(2E
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XX5.4.10. Co-injeções das acil-HS
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Page 137 and 138: PARTE EXPERIMENTAL5. PARTE EXPERIME
Page 139 and 140: PARTE EXPERIMENTAL• Espectroscopi
Page 141 and 142: PARTE EXPERIMENTAL5.1.2. Meios de c
Page 143 and 144: PARTE EXPERIMENTAL5.1.4. Cepas bact
Page 145 and 146: PARTE EXPERIMENTAL(S)-N-heptanoil-h
Page 147 and 148: PARTE EXPERIMENTAL(R)-(+)-N-heptano
Page 149 and 150: PARTE EXPERIMENTAL5.3. Avaliação
Page 151 and 152: PARTE EXPERIMENTALhexano, diclorome
Page 153 and 154: PARTE EXPERIMENTAL4,47 (t, 1H, J 9,
Page 155 and 156: PARTE EXPERIMENTAL13' 11' 9' 7' 5'O
Page 157 and 158: PARTE EXPERIMENTALHinton contendo o
Page 159 and 160: PARTE EXPERIMENTALno caso dos meios
Page 161 and 162: PARTE EXPERIMENTAL(S)-N-tetradecano
Page 163 and 164: PARTE EXPERIMENTALAs acil-HSLs fora
Page 165 and 166: PARTE EXPERIMENTAL5% (2 x 6 mL), bi
Page 167 and 168: PARTE EXPERIMENTAL13'12'11'10'9'8'7
Page 169 and 170: PARTE EXPERIMENTALsinais sobreposto
Page 171 and 172: PARTE EXPERIMENTALóleo e ferveu-se
Page 173 and 174: PARTE EXPERIMENTALRMN de 13 C (75,4
Page 175 and 176: PARTE EXPERIMENTAL(S)-(2E)-N-dodece
Page 177 and 178: PARTE EXPERIMENTAL(S)-3-oxo-(7Z)-N-
Page 179 and 180: PARTE EXPERIMENTAL5.4.9.3. Obtenç
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PARTE EXPERIMENTALIV (KBr): 3318, 3
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PARTE EXPERIMENTALisotermicamente a
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PARTE EXPERIMENTALprocedimento, por
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REFERÊNCIAS BIBLIOGRÁFICAS6. REFE
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REFERÊNCIAS BIBLIOGRÁFICASClusia
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REFERÊNCIAS BIBLIOGRÁFICASENGEBRE
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REFERÊNCIAS BIBLIOGRÁFICASLAMBAIS
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REFERÊNCIAS BIBLIOGRÁFICASusing l
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REFERÊNCIAS BIBLIOGRÁFICASXylella
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