\textfont1=\tenrm \initial \len=4 \newcommand{\rii}{All other argument values cause no action} \newcommand{\rhq}{An argument of ``Q'' causes no action. \ } \subsection{Macros for heterocyclic ring systems} \subsubsection{Macro {\tt\char"5C{}hetthree}[8]} This macro typesets a 3-membered ring with one hetero atom. The common ring structures of this type are epoxides (oxirane) and ethylene imine (aziridine). Ring positions 1, 2, and 3 are the positions to which ${\rm R^1}$, ${\rm R^2}$, and ${\rm R^3}$ are attached. \[ \hetthree{${\rm R^1}$}{${\rm R^2}$}{${\rm R^3}$}{${\rm R^4}$} {Q}{S}{H}{N} \] \begin{description} \item[{\rm Arguments 1--5:}] An argument of ``Q'' causes no action. All other argument values are used as the respective substituent formulas ${\rm R^1}$--${\rm R^5}$. \item[{\rm Argument 6:}] An argument of ``S'' typesets a bond to the left of ring atom \#2. An argument of ``H'' puts ---H to the left of ring atom \#2. For all other argument values, no bond is drawn and ${\rm R^2}$ is moved next to ring atom \#2. \item[{\rm Argument 7:}] An argument of ``S'' typesets a bond to the right of ring atom \#3. An argument of ``H'' puts H--- to the right of ring atom \#3. For all other argument values, no bond is drawn and ${\rm R^3}$ is moved next to ring atom \#3. \item[{\rm Argument 8:}] The atom symbol for the hetero atom. \end{description} \subsubsection{Macro {\tt\char"5C{}hetifive}[9]} This macro typesets 5-membered rings with one hetero atom. Thus it can be used to print the pyrrole, furan, and thiophene ring systems, and their hydrogenated versions. The arguments are selected such that common compounds like proline, pyrrolidone, maleic anhydride, and vitamin C can be printed. Ring positions 1, 2, 3, 4, and 5 are the positions to which ${\rm R^1}$--${\rm R^5}$ are attached. \[ \hetifive{$R^1$}{$R^2$}{$R^3$}{$R^4$}{$R^5$}{D}{Q}{D}{$N$} \hspace{3cm} \hetifive{Q}{O}{Q}{Q}{O}{Q}{D}{Q}{O} \] \begin{description} \item[{\rm Arguments 1,3,4:}] An argument of ``Q'' causes no action. All other argument values are used as the respective substituent formulas ${\rm R^1}$, ${\rm R^3}$, and ${\rm R^4}$. \item[{\rm Argument 2:}] An argument value of ``Q'' causes no action. An argument value of ``O'' puts an outside double bond with an O in ring position 2. All other argument values are used as the substituent formula ${\rm R^2}$ with a single bond. \item[{\rm Argument 5:}] An argument value of ``Q'' causes no action. An argument value of ``O'' puts an outside double bond with an O in ring position 5. All other argument values are used as the substituent formula ${\rm R^5}$ with a single bond. \item[{\rm Argument 6:}] An argument of ``D'' draws a second bond between ring positions 2 and 3. \rii . \item[{\rm Argument 7:}] An argument of ``D'' draws a second bond between ring positions 3 and 4. \rii . \item[{\rm Argument 8:}] An argument of ``D'' draws a second bond between ring positions 4 and 5. \rii . \item[{\rm Argument 9:}] The atomic symbol of the hetero atom. \end{description} \subsubsection{Macro {\tt\char"5C{}heticifive}[9]} This macro typesets a 5-membered ring with 2 hetero atoms separated by a carbon atom. Thus it can be used to print ring systems such as imidazole, thiazole, and oxazole. The arguments were selected by considering actually occurring compounds containing these ring systems. Ring positions 1, 2, 3, 4, and 5 are the positions to which ${\rm R^1}$--${\rm R^5}$ are attached. \[ \heticifive{$R^1$}{$R^2$}{$R^3$}{$R^4$}{$R^5$}{Q}{$R^7$} {$N$}{$N$} \hspace{3cm} \heticifive{Q}{O}{Q}{Q}{Q}{Q}{D}{N}{O} \] \begin{description} \item[{\rm Arguments 1, 3, 5:}] An argument of ``Q'' causes no action. All other argument values are used as the respective substituent formulas ${\rm R^1}$, ${\rm R^3}$, and ${\rm R^5}$. \item[{\rm Argument 2:}] An argument of ``Q''causes no action. An argument of ``O'' puts an outside double bond with an O in ring position 2. All other argument values are used as the substituent formula ${\rm R^2}$ with a single bond. \item[{\rm Argument 4:}] An argument of ``Q''causes no action. An argument of ``O'' puts an outside double bond with an O in ring position 4. All other argument values are used as the substituent formula ${\rm R^4}$ with a single bond. \item[{\rm Argument 6:}] An argument of ``D'' draws a second bond between ring positions 2 and 3. \rii . \item[{\rm Argument 7:}] An argument of ``Q'' causes no action. An argument of ``D'' draws a second bond between ring positions 4 and 5. All other argument values are used as the substituent formula ${\rm R^7}$, the second substituent at ring position 5. \item[{\rm Arguments 8 and 9:}] The atomic symbols of the hetero atoms in position 1 and 3, respectively. \end{description} \subsubsection{Macro {\tt\char"5C{}pyrazole}[8]} The pyrazole ring is found in a number of drugs, such as aminopyrine. Ring positions 1, 2, 3, 4, and 5 are the positions to which ${\rm R^1}$--${\rm R^5}$ are attached. \yi=200 \pht=750 \[ \pyrazole{$R^1$}{$R^2$}{$R^3$}{$R^4$}{$R^5$}{Q}{D}{Q} \hspace{3cm} \pyrazole{$R^1$}{Q}{Q}{Q}{O}{D}{Q}{Q} \] \reinit \begin{description} \item[{\rm Arguments 1, 2, 4:}] An argument of ``Q'' causes no action. All other argument values are used as the respective substituent formulas ${\rm R^1}$, ${\rm R^2}$, and ${\rm R^4}$. \item[{\rm Argument 3:}] An argument of ``Q'' causes no action. An argument of ``O'' puts an outside double bond with an O in ring position 3. All other argument values are used as the substituent formula ${\rm R^3}$ with a single bond. \item[{\rm Argument 5:}] An argument of ``Q'' causes no action. An argument of ``O'' puts an outside double bond with an O in ring position 5. All other argument values are used as the substituent formula ${\rm R^5}$ with a single bond. \item[{\rm Arguments 6, 7, 8:}] An argument of ``D'' draws a second bond between ring positions 2 and 3, ring positions 3 and 4, and ring positions 4 and 5, respectively. \rii . \end{description} \subsubsection{Macro {\tt\char"5C{}hetisix}[9]} This macro typesets a six-membered ring with one hetero atom. Thus it can be used to print ring systems such as pyridine and pyran. The arguments were selected by considering actually occurring compounds such as the B vitamins niacin and pyridoxine and the coumarin ring system. Ring positions 1--6 are the positions to which ${\rm R^1}$--${\rm R^6}$ are attached. \[ \hetisix{$R^1$}{$R^2$}{$R^3$}{$R^4$}{$R^5$}{$R^6$} {D}{D}{$N$} \hspace{3cm} \hetisix{Q}{Q}{Q}{Q}{Q}{Q}{$R^7$}{Q}{O} \] \begin{description} \item[{\rm Argument 1:}] An argument of ``Q'' causes no action. An argument of ``D'' prints a second bond between positions 1 and 6. All other arguments values are used as the substituent formula ${\rm R^1}$. \item[{\rm Arguments 2--6:}] An argument of ``Q'' causes no action. All other argument values are used as the respective substituent formulas ${\rm R^2}$--${\rm R^6}$. \item[{\rm Argument 7:}] An argument of ``Q'' causes no action. An argument of ``D'' prints a second bond between positions 2 and 3. All other argument values cause an outside double bond to be drawn from position 2 and the argument itself to be put at the end of the double bond as ${\rm R^7}$. \item[{\rm Argument 8:}] An argument of ``D'' prints a second bond between positions 4 and 5. \rii . \item[{\rm Argument 9:}] The atomic symbol of the hetero atom. \end{description} \subsubsection{Macro {\tt\char"5C{}pyrimidine}[9]} The pyrimidine ring occurs in such important compounds as cytosine, thymine, uracil, and the barbiturates. The arguments of the macro were selected such that these compounds can be typeset. Ring positions 1--6 are the positions to which ${\rm R^1}$--${\rm R^6}$ are attached. \[ \pyrimidine{$R^1$}{$R^2$}{$R^3$}{$R^4$}{$R^5$}{$R^6$} {Q}{Q}{D} \hspace{3cm} \pyrimidine{$H$}{O}{$H$}{O}{$R^5$}{O}{Q}{$R^8$}{Q} \] \begin{description} \item[{\rm Arguments 1, 3, 5:}] An argument of ``Q'' causes no action. All other argument values are used as the respective substituent formulas ${\rm R^1}$, ${\rm R^3}$, and ${\rm R^5}$. \item[{\rm Argument 2:}] An argument of ``Q'' causes no action. An argument of ``O'' causes an outside double bond with an O to be drawn at position 2. All other argument values are used as the substituent formula ${\rm R^2}$ with a single bond. \item[{\rm Argument 4:}] An argument of ``Q'' causes no action. An argument of ``O'' causes an outside double bond with an O to be drawn at position 4. All other argument values are used as the substituent formula ${\rm R^4}$ with a single bond. \item[{\rm Argument 6:}] An argument of ``Q'' causes no action. An argument of ``O'' causes an outside double bond with an O to be drawn at position 6. All other argument values are used as the substituent formula ${\rm R^6}$ with a single bond. \item[{\rm Argument 7:}] An argument of ``D'' prints a second bond between positions 1 and 2. \rii . \item[{\rm Argument 8:}] An argument of ``Q'' causes no action. An argument of ``D'' prints a second bond between positions 3 and 4. All other argument values are used as the second substituent in position 5, ${\rm R^8}$. \item[{\rm Argument 9:}] An argument of ``D'' prints a second bond between positions 5 and 6. \rii . \end{description} \subsubsection{Macro {\tt\char"5C{}pyranose}[9]} This macro was developed specifically for monosaccharide structures. Carbon \#1 is at the position to which ${\rm R^1}$ is attached. Structures from this macro look best with substituent formulas in 10 point size (shown) or even smaller. \[ \pyranose{$R^1$}{$R^2$}{$R^3$}{$R^4$}{$R^5$}{$R^6$} {$R^7$}{$R^8$}{$R^9$} \] Arguments 1--9 are used as the respective substituent formulas ${\rm R^1}$--${\rm R^9}$. \rhq \subsubsection{Macro {\tt\char"5C{}furanose}[8]} This macro was also developed specifically for monosaccharide structures. Carbon \#1 is at the position to which ${\rm R^1}$ is attached. Structures look best with substituent formulas in 10 point size (shown) or even smaller. \[ \furanose{$R^1$}{$R^2$}{$R^3$}{$R^4$}{$R^5$}{$R^6$} {$R^7$}{$R^8$} \] \begin{description} \item[{\rm Argument 1:}] \rhq An argument of ``N'' prints a long vertical bond at position 1, used for attachment to purine and pyrimidine bases to form nucleosides. All other argument values are used as the substituent formula ${\rm R^1}$. \item[{\rm Arguments 2--8}] \rhq All other argument values are used as the respective substituent formulas ${\rm R^2}$--${\rm R^8}$. \end{description} \subsubsection{Macro {\tt\char"5C{}purine}[9]} The purine ring system occurs in such important compounds as adenine, guanine, caffeine, and uric acid. The arguments of the macro were selected such that these compounds can be typeset. Positions 1, 2, 3, 6, 7, 8, and 9 are indicated in the following diagram by the respective substituent formulas. \[ \purine{$R^1$}{$R^2$}{$R^3$}{Q}{$R^6$}{Q}{$R^7$} {$R^8$}{$R^9$} \] \begin{description} \item[{\rm Arguments 1, 3, 6, 7, 9:}] \rhq All other argument values are used as the respective substituent formulas ${\rm R^1}$ $\ldots$ ${\rm R^9}$. \item[{\rm Argument 2:}] An argument of ``D'' prints a second bond between positions 2 and 3. All other argument values cause an outside double bond to be printed at position 2 and the argument itself to be put at the end of the double bond as the substituent formula ${\rm R^2}$. \item[{\rm Argument 4:}] An argument of ``D'' prints a second bond between positions 1 and 6. \rii . \item[{\rm Argument 5:}] \rhq All other argument values cause an outside double bond to be printed at position 6 and the argument itself to be put at the end of the double bond as the substituent formula ${\rm R^6}$. \item[{\rm Argument 8:}] An argument of ``D'' prints a second bond between positions 7 and 8. All other argument values cause an outside double bond to be printed at position 8 and the argument itself to be put at the end of the double bond as the substituent formula ${\rm R^8}$. \end{description}